Ammonia → HCID 67082406, compound

Participants

Reaction Steps

Lithium aluminum hydride (0.45 g) was suspended in THF (100 ml). The compound (40) (7.5 g) dissolved in THF (100 ml) was added dropwise to this suspension in the temperature range of −20° C. to −10° C., and the mixture was stirred in this temperature range for another 2 hours. After the termination of the reaction had been confirmed by GC analysis, ethyl acetate and a saturated aqueous solution of ammonia were sequentially added to the reaction mixture under ice-cooling, and deposits were removed by filtration through Celite. The filtrate was extracted in ethyl acetate. The organic phase obtained was washed sequentially with water and saturated brine, and then dried over anhydrous magnesium sulfate. Then, the product was purified by means of recrystallization from heptane, dried and concentrated under reduced pressure, giving 7.4 g of 4-hydroxymethyl-[4-pentyl-(2,3-difluorophenyl)cyclohexyl]-cyclohexane (41). The yield based on the compound (40) was 98.1%.

Provenance & Evidence