Isopropyl chloroformate → HCID 57619803, compound

Participants

Reaction Steps

A solution of (3aR,7aS)-1-[1-(4-methyl-4-piperidyl)-4-piperidyl]-3a,4,5,6,7,7a-hexahydro-3H-indol-2-one (100 mg, 0.31 mmol) and triethylamine (0.044 mL, 0.31 mmol) in dichloromethane (5 mL) was added with isopropyl chloroformate (0.313 mL, 1M solution in toluene, 0.31 mmol) dropwise at 0° C. and stirred for 2 hours. Diluted with dichloromethane (60 mL) and 1 N NaOH (10 mL) was added. The phases were separated and aqueous phase was extracted with dichloromethane (2×15 mL). The combined organic phases were washed with brine, concentrated in vacuo and the residue was purified by preparative LC/MS (high pH) to provide the title compound (63 mg, 49.6%). 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 0.85 (s, 3H), 1.19 (d, J=6.25 Hz, 6H), 1.21-1.43 (m, 6H), 1.48-1.87 (m, 10H), 1.87-2.00 (m, 1H), 2.04-2.18 (m, 2H), 2.28 (d, J=6.64 Hz, 1H), 2.32 (d, J=7.03 Hz, 1H), 2.88 (t, J=12.70 Hz, 2H), 2.97 (t, J=8.59 Hz, 1H), 3.20-3.35 (m, 2H), 3.39-3.58 (m, 2H), 3.90 (t, J=12.30 Hz, 1H), 4.76-4.93 (m, 1H). MS (M+1): 406.2.

Provenance & Evidence