Trifluoroacetic acid methylene chloride → (2R,3R)-[3-(tert-Butyldimethylsilanyloxy)-2-methylpyrrolidin-2-yl]methanol trifluoroacetic acid salt

HRID 501606Notes

Reaction equation

HRID 501606 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@:9]1([CH2:22][OH:23])[CH3:21])=O)(C)(C)C.[C:24]([OH:30])([C:26]([F:29])([F:28])[F:27])=[O:25].C(Cl)Cl>>[F:27][C:26]([F:29])([F:28])[C:24]([OH:30])=[O:25].[Si:14]([O:13][C@@H:10]1[CH2:11][CH2:12][NH:8][C@@:9]1([CH2:22][OH:23])[CH3:21])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68457239(2R,3R)-3-(tert-Butyldimethylsilanyloxy)-2-hydroxymethyl-2-methylpyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68459451(2R,3R)-[3-(tert-Butyldimethylsilanyloxy)-2-methylpyrrolidin-2-yl]methanol trifluoroacetic acid salt

Procedure

(2R,3R)-3-(tert-Butyldimethyl-silanyloxy)-2-hydroxymethyl-2-methylpyrrolidine-1-carboxylic acid tert-butyl ester (58B) (269 mg, 0.78 mmol) was stirred in 17% TFA/CH2Cl2 (6 mL) for 30 min. The reaction was concentrated to provide a brown oil (334 mg). LC/MS m/z 246 [M+H]+

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-0b28d35045e4436f8c9c0593492b1af0
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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