(4S,8S,10aS)-4-amino-8-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one → (4S,7R,10aS)-4-Amino-7-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one

Participants

Reaction Steps

(4S,7R,10aS)-4-Amino-7-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one (39 mg, 0.15 mmol) was synthesized as described for the preparation of Intermediate 58 using 5-amino-6,6,6-trifluorohexan-1-ol in step A followed by the preparation of Intermediate 60. Anal. Calcd. for C10H15F3N2OS m/z 268.3. found: 269.0 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 5.29 (dd, J=4.4, 2.8 Hz, 1H), 5.13-4.99 (m, 1H), 3.95 (dd, J=10.6, 3.6 Hz, 1H), 3.07 (ddd, J=14.5, 10.0, 3.3 Hz, 1H), 2.74 (ddd, J=14.6, 6.7, 3.3 Hz, 1H), 2.48-2.29 (m, 2H), 2.24 (ddt, J=13.8, 6.9, 3.4 Hz, 1H), 2.16-2.02 (m, 2H), 1.94-1.69 (m, 5H).

Provenance & Evidence