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Basic Information

Molecular Structure:
CAS No.:	253129-03-2
Name:	(3r,4r)-1-benzyl-4-hydroxy-3-pyrrolidinemethanol
Article Data:	10

Formula:	C12H17 N O2
Molecular Weight:	207.272
Synonyms:	(3r,4r)-1-benzyl-4-hydroxy-3-pyrrolidinemethanol
Density:	1.194g/cm³
Melting Point:	60-62 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
Boiling Point:	336.679°C at 760 mmHg
Flash Point:	167.584°C
PSA:	43.70000
LogP:	0.40950

Synthetic route

: 871086-00-9
(3S,4R)-1-benzyl-4-hydroxy-5-oxopyrrolidine-3-carboxylic acid

: 253129-03-2
(3R, 4R)-1-benzyl-4-(hydroxymethyl)pyrrolidin-3-ol

Conditions

Conditions	Yield
With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran	99%
With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at 20℃; for 72h; pH=7.5;
Multi-step reaction with 2 steps 1: dimethylsulfide borane complex / tetrahydrofuran / -10 - 67 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C View Scheme

: (3R,4R)-(1-benzyl-4-(hydroxymethyl)pyrrolidin-3-ol)borane

: 253129-03-2
(3R, 4R)-1-benzyl-4-(hydroxymethyl)pyrrolidin-3-ol

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 24h;	80%
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / methanol 2: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 15 h / 20 °C / Inert atmosphere View Scheme

: 849935-77-9
ethyl (3S,4R)-1-benzyl-4-hydroxypyrrolidine-3-carboxylate

: 253129-03-2
(3R, 4R)-1-benzyl-4-(hydroxymethyl)pyrrolidin-3-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether	73%
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 20℃; for 1h; Product distribution / selectivity;	73%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h;	71%
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 1h; Product distribution / selectivity;

: ethyl rel-(3R,4S)-1-benzyl-4-hydroxypyrrolidine-3-carboxylate

: 253129-03-2
(3R, 4R)-1-benzyl-4-(hydroxymethyl)pyrrolidin-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 2.53 g / Novozyme(R) 435 lipase from Candida antarctica / various solvent(s) / 2.5 h / 40 °C 2: 73 percent / LiAlH4 / diethyl ether; tetrahydrofuran View Scheme
Multi-step reaction with 2 steps 1: lipase from Candida antarctica / tert-butyl methyl ether / 2.5 h / 40 °C / Enzymatic reaction 2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C View Scheme

: 100-39-0
benzyl bromide

: 267421-93-2
(3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine

: 253129-03-2
(3R, 4R)-1-benzyl-4-(hydroxymethyl)pyrrolidin-3-ol

Conditions

Conditions	Yield
With triethylamine In ethanol at 0 - 20℃; for 1h;
With triethylamine In ethanol at 20℃; for 1h; Cooling with salt-ice bath;

: (+/-)-cis-diethyl 2-benzylisoxazolidine-4,5-dicarboxylate

: 253129-03-2
(3R, 4R)-1-benzyl-4-(hydroxymethyl)pyrrolidin-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; zinc / 20 °C / Cooling with ice 2: Candida antarctica lipase type B / acetone / 24 h / 30 °C / pH 7.5 / aq. phosphate buffer 3: dimethylsulfide borane complex / tetrahydrofuran / -10 - 67 °C View Scheme
Multi-step reaction with 4 steps 1: acetic acid; zinc / 20 °C / Cooling with ice 2: Candida antarctica lipase type B / acetone / 24 h / 30 °C / pH 7.5 / aq. phosphate buffer 3: dimethylsulfide borane complex / tetrahydrofuran / -10 - 67 °C 4: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 15 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: acetic acid; zinc / 20 °C / Cooling with ice 2: Candida antarctica lipase type B / acetone / 24 h / 30 °C / pH 7.5 / aq. phosphate buffer 3: dimethylsulfide borane complex / tetrahydrofuran / -10 - 67 °C 4: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: acetic acid; zinc / 20 °C / Cooling with ice 2: Candida antarctica lipase type B / acetone / 24 h / 30 °C / pH 7.5 / aq. phosphate buffer 3: dimethylsulfide borane complex / tetrahydrofuran / -10 - 67 °C 4: palladium 10% on activated carbon; hydrogen / methanol 5: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 15 h / 20 °C / Inert atmosphere View Scheme

: 871086-00-9
(3S,4R)-1-benzyl-4-hydroxy-5-oxopyrrolidine-3-carboxylic acid

A: 253129-03-2
(3R, 4R)-1-benzyl-4-(hydroxymethyl)pyrrolidin-3-ol

B: (3R,4R)-(1-benzyl-4-(hydroxymethyl)pyrrolidin-3-ol)borane

Conditions

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran at -10 - 67℃;

: 3376-26-9
N-Benzylidenebenzylamine N-oxide

: 253129-03-2
(3R, 4R)-1-benzyl-4-(hydroxymethyl)pyrrolidin-3-ol

Conditions

Yield

Multi-step reaction with 5 steps
1.1: hydrogenchloride / water / 70 °C
2.1: sodium acetate / ethanol / 1 h / 20 °C
2.2: 1 h / 20 °C
2.3: 2.5 h / Reflux
3.1: acetic acid; zinc / 20 °C / Cooling with ice
4.1: Candida antarctica lipase type B / acetone / 24 h / 30 °C / pH 7.5 / aq. phosphate buffer
5.1: dimethylsulfide borane complex / tetrahydrofuran / -10 - 67 °C
View Scheme

Multi-step reaction with 6 steps
1.1: hydrogenchloride / water / 70 °C
2.1: sodium acetate / ethanol / 1 h / 20 °C
2.2: 1 h / 20 °C
2.3: 2.5 h / Reflux
3.1: acetic acid; zinc / 20 °C / Cooling with ice
4.1: Candida antarctica lipase type B / acetone / 24 h / 30 °C / pH 7.5 / aq. phosphate buffer
5.1: dimethylsulfide borane complex / tetrahydrofuran / -10 - 67 °C
6.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C
View Scheme

: 29601-98-7
N-benzylhydroxylamine hydrochloride

: 253129-03-2
(3R, 4R)-1-benzyl-4-(hydroxymethyl)pyrrolidin-3-ol

Conditions

Yield

Multi-step reaction with 4 steps
1.1: sodium acetate / ethanol / 1 h / 20 °C
1.2: 1 h / 20 °C
1.3: 2.5 h / Reflux
2.1: acetic acid; zinc / 20 °C / Cooling with ice
3.1: Candida antarctica lipase type B / acetone / 24 h / 30 °C / pH 7.5 / aq. phosphate buffer
4.1: dimethylsulfide borane complex / tetrahydrofuran / -10 - 67 °C
View Scheme

Multi-step reaction with 5 steps
1.1: sodium acetate / ethanol / 1 h / 20 °C
1.2: 1 h / 20 °C
1.3: 2.5 h / Reflux
2.1: acetic acid; zinc / 20 °C / Cooling with ice
3.1: Candida antarctica lipase type B / acetone / 24 h / 30 °C / pH 7.5 / aq. phosphate buffer
4.1: dimethylsulfide borane complex / tetrahydrofuran / -10 - 67 °C
5.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C
View Scheme

: 71336-69-1, 71336-70-4
(+/-)-trans-ethyl 1-benzyl-4-hydroxy-5-oxopyrrolidine-3-carboxylate

: 253129-03-2
(3R, 4R)-1-benzyl-4-(hydroxymethyl)pyrrolidin-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Candida antarctica lipase type B / acetone / 24 h / 30 °C / pH 7.5 / aq. phosphate buffer 2: dimethylsulfide borane complex / tetrahydrofuran / -10 - 67 °C View Scheme
Multi-step reaction with 3 steps 1: Candida antarctica lipase type B / acetone / 24 h / 30 °C / pH 7.5 / aq. phosphate buffer 2: dimethylsulfide borane complex / tetrahydrofuran / -10 - 67 °C 3: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 15 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: Candida antarctica lipase type B / acetone / 24 h / 30 °C / pH 7.5 / aq. phosphate buffer 2: dimethylsulfide borane complex / tetrahydrofuran / -10 - 67 °C 3: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: Candida antarctica lipase type B / acetone / 24 h / 30 °C / pH 7.5 / aq. phosphate buffer 2: dimethylsulfide borane complex / tetrahydrofuran / -10 - 67 °C 3: palladium 10% on activated carbon; hydrogen / methanol 4: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 15 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: Novozyme 435 / pH 7.4 / Enzymatic reaction 2: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran View Scheme