Acetone → HCID 67323975, compound

Participants

Reaction Steps

7-(Phenylsulfonyl)-1,2,3,3a,4,9b-hexahydrochromeno[3,4-b]pyrrole hydrochloride (enantiomer 1, Example 55, 20 mg, 0.08 mmol) was dissolved in 500 μL DCE:MeOH (9:1). After 10 min stirring, propan-2-one (7 μL, 1.5 eq), a 1 M solution of sodium cyanoborohydride in THF (0.16 mL, 0.16 mmol) and acetic acid (50 μL) were added sequentially. After stirring for 16 h, the reaction mixture was passed through a plug of silica gel and the solvent was evaporated. The residue was purified by preparative LC/MS using the standard procedure. The resulting material was dissolved in a small amount of DCM, treated with 1.0 N HCl in diethyl ether and the solvent evaporated to provide 7-(phenylsulfonyl)-3-(propan-2-yl)-1,2,3,3a,4,9b-hexahydrochromeno[3,4-b]pyrrole hydrochloride. MS m/z 358.1 [M+H]+. 1H-NMR (400 MHz, DMSO-d6): δ 1.30 (d, J=1.6 Hz, 3H), 1.35 (d, J=1.6 Hz, 3H), 1.83-1.88 (m, 1H), 2.62-2.66 (m, 1H), 3.21-3.24 (m, 1H), 3.37 (bs, 1H), 3.66-3.72 (m, 2H), 4.10-4.24 (m, 3H), 4.23-4.41 (m, 1H), 7.45 (s, 1H), 7.52-7.77 (m, 5H), 7.97 (d, J=2 Hz 1H), 10.4 (bs, 1H).

Provenance & Evidence