Water → (2S,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid (4-trifluoromethoxy-phenyl)-amide

HRID 455252Notes

Reaction equation

HRID 455252 reaction equation
[BH4-].[Na+].C[O:4][C:5]([C@@H:7]1[CH2:11][C@@H:10]([O:12][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][N:8]1[C:30](=[O:43])[NH:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][C:39]([F:42])([F:41])[F:40])=[CH:34][CH:33]=1)=O.O>CO>[F:42][C:39]([F:40])([F:41])[O:38][C:35]1[CH:36]=[CH:37][C:32]([NH:31][C:30]([N:8]2[CH2:9][C@H:10]([O:12][Si:13]([C:26]([CH3:27])([CH3:28])[CH3:29])([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11][C@H:7]2[CH2:5][OH:4])=[O:43])=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 70975932(2S,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-(4-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 71020558(2S,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid (4-trifluoromethoxy-phenyl)-amideYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (200 mg, 5.3 mmol) was added to a solution of (2S,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-(4-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-2-carboxylic acid methyl ester (2.8 g, 4.8 mmol) in methanol (50 mL) portion-wise. The mixture was stirred at room temperature for 4 hours. Then the mixture was poured into water (50 mL), extracted with ethyl acetate (3×50 mL). The organic layers was combined, washed with brine (50 mL), dried over anhydrous sodium sulphate, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=5:1) to give 2.35 g (88%) of the title compound.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washwashed with brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-b4106813de8f4999af65c9d99897739e
Source dataset
uspto-grants-2013_07
Patent number
US08497288B2

Reaction notes

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