Cornforth reagent → HCID 69926974, compound

HRID 1280733Notes

Reaction equation

HRID 1280733 reaction equation
[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])([CH3:3])[CH3:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[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])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 69969029HCID 69969029, compound

Product 1

HCID 69926974HCID 69926974, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3RS,4RS)-3-(4-Benzyloxy-benzenesulfonyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (50 mg, 0.1 mmol) was dissolved in CH2Cl2 (2 ml) and treated successively with 4 Å molecular sieves (56 mg, powder) and pyridinium dichromate (56.4 mg, 0.15 mmol). After 3 hours stirring at room temperature, the reaction mixture was directly chromatographed over silica gel (hexane-ethyl acetate 4:1 then 1:1) to provide (RS)-3-(4-benzyloxy-benzenesulfonyl)-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (27 mg, 48%) as an oil, MS: m/e=374.2 (M-tbutyl).

Workup

  1. customthe reaction mixture was directly chromatographed over silica gel (hexane-ethyl acetate 4:1

Sources & evidence

ORD record
ord-0311a57a7ba74c1a9ee14d6ff095083c
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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