Hydrochloric Acid → HCID 69969029, compound

HRID 1280732Notes

Reaction equation

HRID 1280732 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[O:13])[CH:10]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].Cl>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([OH:13])[CH:10]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 69926974HCID 69926974, compound

Product 1

HCID 69969029HCID 69969029, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

(RS)-3-(4-Benzyloxy-benzenesulfonyl)-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (13.4 mg, 0.031 mmol) was dissolved in MeOH (0.5 ml), cooled to 0° C. and treated with NaBH4 (1.64 mg, 0.043 mmol). After 0.5 hour stirring at 0° C., the reaction mixture was acidified to pH 1 with 1N HCl. The aqueous phase was extracted with CH2Cl2. The combined organic phases were washed with H2O, dried over Na2SO4, filtered and the solvent was evaporated to provide (3RS,4SR)-3-(4-benzyloxy-benzenesulfonyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (12.3 mg, 92%) as a white solid, MS: m/e=434.4 (M+H+).

Workup

  1. extractionThe aqueous phase was extracted with CH2Cl2
  2. washThe combined organic phases were washed with H2O
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-87f367d4b9db4ebcaaf5ec55e96c10c5
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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