Cyclohexene oxide → HCID 44160187, compound

Participants

Reaction Steps

2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (1 gm, 5 mmol) was taken in DMF (10 ml). NaH (300 mg, 12.5 mmol) was added to it and the reaction mixture stirred at RT for 15 min. 7-oxabicyclo[4.1.0]heptane (0.9 ml, 9.0 mmol) was taken in DMF (3 ml) and added drop wise to the reaction mixture. After complete addition, reaction mixture was heated at 60-65° C. overnight. The reaction was monitored by LCMS. After completion of the reaction, reaction mixture was cooled to RT and quenched with water, extracted with ethyl acetate (3×25 ml), dried over sodium sulfate and concentrated under vacuum to obtain the crude product. This crude was purified by silica gel column chromatography (Eluent: 20% Methanol in DCM) to get 900 mg of 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)cyclohexanol as yellow semi solid. 1H NMR (CDCl3) FREE BASE 7.37-7.30 (m, 2H), 7.20 (s, 1H), 4.37-4.22 (bs, 1H), 3.67-3.64 (s, 1H), 3.61-3.57 (m, 2H), 3.0-2.80 (m, 3H), 2.60-2.40 (m, 7H), 1.98-1.82 (m, 4H), 1.50-1.38 (m, 4H).

Provenance & Evidence