Methanol → HCID 22229149, compound

Participants

Reaction Steps

This example describes the preparation of I where n=2 and R1=n-propyl. In a nitrogen-filled glove box, a Fisher-Porter tube was charged with iridium catalyst prepared as in Example 1 (8 mg, 0.010 mmol) and 3-(butylidene)-2-piperidone (150 mg, 1.0 mmol). Methanol (2 mL) and dichloromethane (2 mL) were added and the system was flushed 4 times with hydrogen and pressured to 60 psi (0.5 Mpa) H2. After 18 h the reaction mixture was filtered through a short pad of silica. The solvent was removed at reduced pressure to afford 3-butyl-2-piperidone (140 mg, 93%) as a white crystalline solid. Chiral gas chromatographic analysis (Rt-GammaDex SA column, 130° C. for 5 min, then programmed to 200° C. at 10°/min) indicated that conversion was 95% and the enantiomeric excess was 90%. 13C NMR: δ 14.24, 21.27, 22.85, 26.04, 29.25, 31.36, 40.96, 42.38, 176.02; 1H NMR: δ 0.91 (t, J=7, 3H), 1.22-1.58 (m, 6H), 1.70 (m, 1H), 1.79-2.00 (m, 3H), 2.24 (m, 1H), 3.29 (m, 2H), 7.25 (br s, 1H).

Provenance & Evidence