Dicyclohexylcarbodiimide → 1-[(2S,4R,5S)-5-octyl-4-methyl-1,3-dioxan-2-yl]-4-[(S)-2-fluorohexanoyloxy]benzene

Participants

Reaction Steps

A mixture of 380 mg of 4-[(2S,4R,5S)-5-octyl-4-methyl-1,3-dioxan-2-yl]phenol, 185 mg of (S)-2-fluorocaproic acid, 333 mg of N,N'-dicyclohexylcarbodiimide, 20 mg of 4-(dimethylamino)pyridine and 40 ml methylene chloride was stirred at room temperature under nitrogen for 16.5 hours. Subsequently, the suspension was filtered and the filtrate was evaporated on a rotary evaporator. The crude product (1.0 g) was suspended in 50 ml of methylene chloride, the suspension was filtered and the filtrate was evaporated. Recrystallization of the white, solid residue (0.5 g) from hexane gave 0.4 g of 0.4 g of 1-[(2S,4R,5S)-5-octyl-4-methyl-1,3-dioxan-2-yl]-4-[(S)-2-fluorohexanoyloxy]benzene as white crystals with m.p. (C-I) 58.8° C. and [a]D =+16.7° (c=1% in chloroform).

Provenance & Evidence