3-Pyridinecarboxaldehyde → 2-Allyl-1-(3-pyridyl)-1,3-propanediol

Participants

Reaction Conditions

Reaction Steps

A 1M solution of dibutylboron triflate in dichloromethane (32.7 ml) was added to a solution of A (6.28 g) in dry dichloromethane (110 ml), cooled to 5° C. under argon, followed by diisopropylethylamine (6.25 ml). The reaction mixture was stirred at 5° C. for 30 minutes and then cooled to -78° C. 3-Pyridinecarboxaldehyde (3.1 ml) was added dropwise. The mixture was stirred for 30 minutes at -78° C., and then allowed to warm to -50° C. over 30 minutes. The cooling bath was removed and the reaction mixture was stirred at room temperature for 2 hours. The mixture was then cooled to 5° C. and hydrogen peroxide (11.5 ml, 30% w/v aqueous solution) was added. The mixture was stirred for 30 minutes and then poured into water (50 ml) and extracted with dichloromethane (3×100 ml). The combined extracts were dried (MgSO4) and evaporated. The residue was purified by flash column chromatography, eluting with ethyl acetate/hexane (1:1 v/v, gradually increasing to 100% ethyl acetate), to give (4S)-(3-[(2S)-2-[(1S-1-hydroxy-1-(3-pyridyl)methyl]pent-4-enoyl)-4-isopropyloxazolidin-2-one (B), as a solid, m.p. 112°-113° C. (after recrystallisation from toluene); 25 [α]D =+136.0 (EtOH, c 0.311);

Provenance & Evidence