Name: GRT6005
SKU: 863513-91-1

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Basic Information

Molecular Structure:
CAS No.:	863513-91-1
Name:	GRT6005
Article Data:	9

Formula:	C24H27FN2O
Molecular Weight:	378.49
Synonyms:	Cebranopadol;Cebranopadol (USAN/INN);(1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indol]-4-amine;(1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indole]-4-amine;
Density:	1.23±0.1 g/cm3(Predicted)
Boiling Point:	547.5±50.0 °C(Predicted)
PSA:	28.26000
LogP:	5.10610

Synthetic route

: 863513-91-1
(1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indole]-4-amine

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 22 - 40℃; for 65h; Inert atmosphere;	91%
Stage #1: 4-dimethylamino-4-phenylcyclohexanone; 2-(5-fluoro-1H-indol-3-yl)ethanol With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20 - 45℃; for 65h; Inert atmosphere; Stage #2: With sodium hydroxide In dichloromethane; water at 21 - 22℃;	91%
With sulfuric acid In acetic acid at 45 - 60℃;	60%

: 863513-91-1
(1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indole]-4-amine

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride / water; methanol / 0 - 20 °C 2.1: tetrahydrofuran / 0 - 20 °C 2.2: 0 - 20 °C 3.1: water; hydrogenchloride / diethyl ether 4.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 20 h / 20 °C / Inert atmosphere View Scheme

: 863513-91-1
(1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indole]-4-amine

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 0 - 20 °C 1.2: 0 - 20 °C 2.1: water; hydrogenchloride / diethyl ether 3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 20 h / 20 °C / Inert atmosphere View Scheme

: 65619-19-4
4-dimethylamino-4-phenylcyclohexanone, ethylene ketal hydrochloride

: 863513-91-1
(1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indole]-4-amine

Conditions	Yield
Multi-step reaction with 2 steps 1: water; hydrogenchloride / diethyl ether 2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 20 h / 20 °C / Inert atmosphere View Scheme

: 863513-91-1
(1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indole]-4-amine

Conditions	Yield
With formic acid In water at 70℃; for 16h; Eschweiler-Clark Amine Methylation;	280 mg

: 863513-91-1
(1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indole]-4-amine

: 1443039-98-2
(1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indole]-4-amine hydrochloride

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water; acetone at 20℃; for 120h; Concentration; Solvent; Time;
With hydrogenchloride In tetrahydrofuran; water; acetone at 20℃; for 24h;