Benzoyl chloride → HCID 70024926, compound

Participants

Reaction Steps

To an ice cold, stirred solution of (S)-N-benzyl-3-pyrrolidinol (6.90 Kg, 38.9 mole) in dichloromethane (21 L), was slowly added a solution of benzoyl chloride (5.75 Kg, 40.8 mole) in dichloromethane (5 L). The reaction mixture was warmed to room temperature and stirred an additional two hours. Upon confirmation of reaction completion, methyl t-butyl ether (26 L) was added, and the resulting slurry was stirred for two hours at −10° C. The solids were isolated by filtration, washed with methyl t-butyl ether (14 L) and dried under vacuum at 40° C. to provide the title pyrrolidine (11.8 Kg, 96.6%) as a colorless crystalline material. mp 203-204° C.; 1H NMR (400 MHz, CDCl3) (major isomer) δ 8.14-7.90 (m, 2H), 7.70-7.39 (m, 8H), 5.59-5.58 (m, 1H), 4.30 (d, J=5.5 Hz, 2H), 4.14-4.08 (m, 1H), 3.80-3.76 (m, 1H), 3.24-3.17 (m, 2H), 2.66-2.61 (m, 1H), 2.37-2.32 (m, 1H); 13C NMR (100 MHz, CDCl3) δ 166.2, 165.6, 134.0, 133.7, 131.1, 130.9, 130.3, 130.2, 130.1, 130.0, 129.8, 129.6, 129.5, 129.4, 129.1, 129.0, 128.8, 128.6, 73.0, 71.9, 59.1, 58.5, 57.5, 57.2, 52.1, 52.0, 31.3, 30.6; MS [(m+1)/z] 282.2.

Provenance & Evidence