Ammonium Chloride → HCID 66615727, compound

Participants

Reaction Conditions

Reaction Steps

At −10° C., a mixture of (3S,3aS,5R)-3,8-dimethyl-5-(prop-1-en-2-yl)-3,3a,4,5,6,7-hexahydroazulen-1(2H)-one (53 mg, 0.243 mmol) and CeCl3.7H2O (90 mg, 0.243 mmol) in MeOH (5 ml) was treated with sodium borohydride (9.2 mg, 0.243 mg) and the resulting mixture was stirred at 0° C. for 20 min., poured into aqueous saturated NH4Cl solution (5 ml) and ice and extracted twice with diethyl ether (3 ml). The combined organic phases were washed with aqueous saturated NaHCO3 solution (3 ml), with aqueous saturated NaCl solution (3 ml), dried with MgSO4, filtered, and the solvent evaporated. FC (5 g SiO2, hexane/MTBE 10:0.1 to 10:0.2 to 10:0.5) of the crude product (52 mg, GC: 93:7 (1R)/(1S)-epimer) gave (1R,3S,3aS,5R)-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulen-1-ol (34 mg, 64%) and (1 S,3S,3aS,5R)-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulen-1-ol (1 mg, 2%).

Provenance & Evidence