Sodium borohydride → HCID 68154423, compound

Participants

Reaction Conditions

Reaction Steps

202 mg (8R,8aR)-3,4,6,7,8,8a-hexahydro-2H-chromene-8-carbaldehyde was dissolved in 8 mL MeOH and the solution was cooled to 0° C. and 52 mg sodium borohydride was added slowly. The reaction was stirred for several hours and gradually warmed to RT. The methanol was removed using a rotovap and the residue was diluted with CH2Cl2 and added to sat. NH4Cl. The mixture was separated, and the aqueous was extracted with CH2Cl2. The crude extract was dried over Na2SO4, filtered, concentrated, then purified on silica gel to provide the title compound. 1H NMR (400 MHz, CDCl3) δ=1.46-1.80 (m, 4H), 1.84-2.10 (m, 3H), 2.13-2.38 (m, 2H), 2.78-2.86 (m, 1H), 3.52-3.62 (m, 1H), 3.66-3.76 (m, 1H), 3.76-3.87 (m, 1H), 3.94-3.47 (m, 2H), 5.52 (s, 1H) ppm.

Provenance & Evidence