HCID 70024926, compound → HCID 11521463, compound

Participants

Reaction Conditions

Reaction Steps

A warm suspension of (S)-3-Benzoyloxy-N-benzyl-pyrrolidine hydrochloride (11.8 Kg, 37.0 mole) in 2-propanol (118 L) at 40° C. was hydrogenated over 10% palladium on carbon (2.35 Kg, 50% water wet) under 50 psig for 12 hours. Upon confirmation of reaction completion, the mixture was filtered over Celite and the latter was rinsed with additional 2-propanol (38 L). The combined filtrate and rise solutions were concentrated by atmospheric distillation (total volume of 35 L). At this stage, diisopropyl ether (105 L) was slowly added over 15 minutes, and the resulting slurry was further stirred at 55° C. for 15 minutes. The reaction mixture was gradually cooled to −10° C., and stirred an additional 2 hours. The solids were isolated by filtration, washed with diisopropyl ether (30 L) and dried under vacuum at 40° C. to provide the title pyrrolidine (7.3 Kg, 86.6%) as a colorless crystalline material. mp 140-141° C.; 1H NMR (400 MHz, d-6 DMSO) δ 9.65 (bs, s, 2H), 8.04-8.01 (m, 2H), 7.68-7.64 (m, 1H), 7.53-7.49 (m, 2H), 5.53-5.51 (m, 1H), 3.42-3.41 (m, 2H), 3.33-3.28 (m, 2H), 2.25-2.15 (m, 2H); 13C NMR (100 MHz, d-6 DMSO) δ 165.8, 134.3, 130.2, 130.0, 129.3, 74.2, 50.4, 43.7, 31.3; MS [(m+1)/z] 192.2.

Provenance & Evidence