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

Participants

Reaction Steps

(4S,8R,10aS)-4-Amino-8-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one (50 mg, 0.19 mmol) was synthesized as described for the preparation of Intermediate 60 using benzyl (4S,8R,10aS)-5-oxo-8-(trifluoromethyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate. Anal. Calcd. for C10H15F3N2OS m/z 268.2. found: 269.0 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 5.30 (dd, J=5.3, 3.8 Hz, 1H), 4.60 (dd, J=13.4, 4.3 Hz, 1H), 4.06 (dd, J=10.0, 4.2 Hz, 1H), 3.04 (ddd, J=14.3, 9.9, 3.0 Hz, 1H), 2.91 (t, J=12.8 Hz, 1H), 2.66 (ddd, J=14.6, 7.2, 3.1 Hz, 1H), 2.39-2.16 (m, 2H), 2.05 (dddd, J=14.5, 9.7, 7.8, 4.1 Hz, 2H), 1.94-1.85 (m, 1H), 1.80-1.64 (m, 4H).

Provenance & Evidence