Ammonium Chloride → HCID 13964339, compound

Participants

Reaction Steps

64.0 g (110 mmoles) of (1R,2R,3R,4S)-1-t-butyldimethylsilyloxy-2-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-4-hydroxymethyl-3-(3-trimethylsilyl-2-propynyl)cyclopentane (31) was taken into a 1-liter eggplant-shaped flask, and dissolved by adding 500 ml of methanol. Then, 106.3 g of a 28% methanol solution of sodium methylate was added, and the mixture was stirred at room temperature for 30 minutes. Saturated aqueous ammonium chloride solution (300 ml) was added, and the mixture was extracted twice with ethyl acetate. The organic layer was successively washed with saturated aqueous potassium hydrogensulfate solution, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 53.9 g (yield 96%) of (1R,2R,3R,4S)-1-t-butyldimethylsilyloxy-2-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-4-hydroxymethyl-3-(2-propynyl)cyclopentane (32) from eluates obtained with 10% ethyl acetate/n-hexane.

Provenance & Evidence