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

HRID 2375460Notes

Reaction equation

HRID 2375460 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

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 45037029HCID 45037029, compound

Product 1

HCID 26967704tert-Butyl (2S)-4-oxo-2-phenylpyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 minutes. (2S,4S)-tert-Butyl 4-hydroxy-2-phenylpyrrolidine-1-carboxylate (6-2, 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 (2S)-tert-butyl 4-oxo-2-phenylpyrrolidine-1-carboxylate (6-3). Recrystallization was effected with EtOAc/hexanes. 1H NMR (300 MHz, CDCl3) δ 7.35 (m, 3H), 7.17 (m, 2H), 5.38 (m, 1H), 4.08 (d, J=19.5 Hz, 1H), 3.90 (d, J=19.3 Hz, 1H), 3.13 (dd, J=18.8, 9.8 Hz, 1H), 2.58 (dd, J=18.6, 2.4 Hz, 1H), 1.40 (br s, 9H); MS 206.0 found, 206.1 (M−C(CH3)3) required.

Workup

  1. customTo a flame dried flask
  2. customequipped
  3. additionwas added 150 mL anhydrous dichloromethane which
  4. stirringthe reaction stirred for 10 minutes
  5. stirringstirred 1 hour at −78° C
  6. temperaturethe reaction was warmed to 0° C. over 1 hour
  7. washUpon completion, the reaction was washed with 5% NaHCO3, brine
  8. dry with materialdried over MgSO4
  9. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-b1b4612d7bb4437697f3372c67248070
Source dataset
uspto-grants-2008_12
Patent number
US07465746B2

Reaction notes

Loading…