(R)-2-(Bis(3,5-bis(trifluoromethyl)phenyl)((trimethylsilyl)oxy)methyl)pyrrolidine

Base Information

• Chemical Name: (R)-2-(Bis(3,5-bis(trifluoromethyl)phenyl)((trimethylsilyl)oxy)methyl)pyrrolidine
• CAS No.: 908303-26-4
• Molecular Formula: C24H23F12NOSi
• Molecular Weight: 597.519
• European Community (EC) Number: 625-410-2
• DSSTox Substance ID: DTXSID20584872
• Nikkaji Number: J2.863.443I
• Wikidata: Q72444369
• Mol file: 908303-26-4.mol

Synonyms:908303-26-4;(R)-2-(Bis(3,5-bis(trifluoromethyl)phenyl)((trimethylsilyl)oxy)methyl)pyrrolidine;[bis[3,5-bis(trifluoromethyl)phenyl]-[(2R)-pyrrolidin-2-yl]methoxy]-trimethylsilane;(R)-A,a-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether;(2R)-2-[Bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilyl)oxy]methyl]-pyrrolidine;(2R)-2-{Bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilyl)oxy]methyl}pyrrolidine;C24H23F12NOSi;(R)-2-(bis(3,5-bis(trifluoromethyl)phenyl)(trimethylsilyloxy)methyl)pyrrolidine;MOHRGTBNEJKFMB-LJQANCHMSA-N;SCHEMBL3006875;DTXSID20584872;MFCD09750448;AKOS016843318;(R)-Alpha,alpha-bis[3,5-bis-(trifluoromethyl)phenyl]prolinol trimethylsilyl ether;AS-42928;CS-0091969;A860689;(R)- alpha , alpha -Bis[3,5-bis(trifluoromethyl)phenyl]prolinol trimethylsilyl ether;(R)-2-(BIS(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-((TRIMETHYLSILYL)OXY)METHYL)PYRROLIDINE;(R)-alpha,alpha-Bis[3,5-bis(trifluoromethyl)phenyl]prolinol trimethylsilyl ether;R)-,-Bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether;R)-|A,|A-Bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether;(R)-alpha,alpha-Bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether, technical grade

Chemical Property of (R)-2-(Bis(3,5-bis(trifluoromethyl)phenyl)((trimethylsilyl)oxy)methyl)pyrrolidine

Chemical Property:

• Appearance/Colour: White to Off-White Solid
• Vapor Pressure: 4.72E-06mmHg at 25°C
• Melting Point: 56-58oC
• Refractive Index: 1.439
• Boiling Point: 382.4oC at 760 mmHg
• PKA: 9.34±0.10(Predicted)
• Flash Point: 185.1oC
• PSA: 21.26000
• Density: 1.319g/cm3
• LogP: 8.93770
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 5
• Exact Mass: 597.1357288
• Heavy Atom Count: 39
• Complexity: 737

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2R)-2-[Bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilyl)oxy]methyl]-pyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[Si](C)(C)OC(C1CCCN1)(C2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F
• Isomeric SMILES: C[Si](C)(C)OC([C@H]1CCCN1)(C2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F
• Uses: Catalyst involved in:Cyclocondensation of enals with methylenepyrrolidinesOrganocatalytic additions of β-ketosulfoxides to conjugated aldehydesOrganocatalytic aza-Michael reactionsStereoselective propargylic alkylation of propargylic esters with aldehydesEpoxidation or aziridination of α,β-unsaturated aldehydes and Feist-Benary reactions of 1,3-dicarbonyls

Technology Process of (R)-2-(Bis(3,5-bis(trifluoromethyl)phenyl)((trimethylsilyl)oxy)methyl)pyrrolidine

There total 1 articles about (R)-2-(Bis(3,5-bis(trifluoromethyl)phenyl)((trimethylsilyl)oxy)methyl)pyrrolidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + (R)-α,α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol (948595-00-4) → (R)-(-)-α,α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanoltrimethylsilyl ether (908303-26-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol900350k

Reference yield: 100.0%

(R)-(-)-α,α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanoltrimethylsilyl ether (908303-26-4) + phenylacetaldehyde (122-78-1) → C32H29F12NOSi

Guidance literature:

In benzene-d6; at 25 ℃; for 48h; Inert atmosphere; Schlenk technique; Molecular sieve;

DOI:10.1021/jacs.5b01662

Reference yield:

(R)-(-)-α,α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanoltrimethylsilyl ether (908303-26-4) + hexanal (66-25-1) → C30H33F12NOSi

Guidance literature:

In acetonitrile; at 20 ℃; for 0.166667h; Molecular sieve;

DOI:10.1021/acs.orglett.1c02387

upstream raw materials:

trimethylsilyl trifluoromethanesulfonate

(R)-α,α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol

Refernces

• 1、 Lin, Qiyan,Meloni, David,Pan, Yongchun,Xia, Michael,Rodgers, James,Shepard, Stacey,Li, Mei,Galya, Laurine,Metcalf, Brian,Yue, Tai-N,Liu, Pingli,Zhou, Jiacheng. "Enantioselective synthesis of janus kinase inhibitor INCB018424 via an organocatalytic aza-michael reaction". supporting information; experimental part. p. 1999 - 2002. Retrieved 2009/09/06.