Dimethyl Sulfoxide → HCID 58055030, compound

HRID 2383500Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][C@@H:12]1[C@@H:16]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:15][N:14]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:13]1.C(N(CC)CC)C>C(Cl)Cl.O>[Si:18]([O:17][C@@H:16]1[C:12](=[O:11])[CH2:13][N:14]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:15]1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: -45 °C

Procedure

To a solution of oxalyl chloride (0.51 mL) in CH2Cl2 (7.3 mL) was added a 4.0M CH2Cl2 solution of DMSO (0.86 mL) at −78° C. After 10 min, a solution of tert-butyl (3S,4S)-3-hydroxy-4-(tert-butyldimethylsilyl)oxypyrrolidine-1-carboxylate (920 mg) in CH2Cl2 (5.8 mL) was added, and the mixture was stirred for 2 hours at −45° C. Triethylamine (3.25 mL) was added, and after being stirred for 10 min at room temperature, water was added. The mixture was separated, and the aqueous layer was extracted with ether. The combined organic layer was washed with brine, and dried over MgSO4 and concentrated. The residue was purified with silica gel column chromatography (eluent: hexane/EtOAc=1/0˜50/50) to give tert-butyl (3S)-3-(tert-butyldimethylsilyl)oxy-4-oxopyrrolidine-1-carboxylate as a pale yellow foam.

Workup

stirringafter being stirred for 10 min at room temperature
customThe mixture was separated
extractionthe aqueous layer was extracted with ether
washThe combined organic layer was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified with silica gel column chromatography (eluent: hexane/EtOAc=1/0˜50/50)

Sources & evidence

ORD record: ord-c8d5b9e9daa543fb8ebd2751da8f7935
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263632B2

Reaction notes

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