Dimethyl Sulfoxide → tert-Butyl (2S)-4-oxo-2-phenylpyrrolidine-1-carboxylate

HRID 1394938Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][C@@H:12]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:14]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:13]1.C(N(CC)CC)C>ClCCl>[O:11]=[C:12]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:14]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:13]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a flame dried flask equipped with stir bar was added 150 mL anhydrous dichloromethane which was cooled to −78° C. Oxalyl chloride (3.8 mL, 44 mmol) and DMSO (4.8 mL, 61 mmol) were added sequentially and the reaction stirred for 10 min. tert-butyl(2S,4S)-4-hydroxy-2-phenylpyrrolidine-1-carboxylate (5-2, 2.28 g, 8.73 mmol) in 10 mL anhydrous dichloromethane was added dropwise and stirred 1 hour at −78° C. Triethylamine (12 mL, 87 mmol) was added and the reaction was warmed to 0° C. over 1 hour. Upon completion, the reaction was washed with 5% NaHCO3, brine and dried over MgSO4. The organic layer was concentrated to provide crude tert-butyl(2S)-4-oxo-2-phenylpyrrolidine-1-carboxylate (5-3).

Workup

customTo a flame dried flask
customequipped
additionwas added 150 mL anhydrous dichloromethane which
additionwas added dropwise
stirringstirred 1 hour at −78° C
temperaturethe reaction was warmed to 0° C. over 1 hour
washUpon completion, the reaction was washed with 5% NaHCO3, brine
dry with materialdried over MgSO4
concentrationThe organic layer was concentrated

Sources & evidence

ORD record: ord-dd5a26c493fe439989dbdd1c7eb83bc1
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348440B2

Reaction notes

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