HCID 10023610, compound → (S)-6-Benzyloxy-2-methyl-hexan-1-ol

Participants

Reaction Conditions

Reaction Steps

To a suspension of 13.2 g (0.35 mol) of LiAlH4 in 380 ml of THF was added a solution of amide VI in 250 ml of THF at 0° C. The mixture was stirred for 2 h at 0° C. and quenched with 14 ml of H2O, 14 ml of 15% NaOH and 25 ml of H2O. The precipitated aluminum salts were removed by filtration. After concentration of the filtrate, the crude product was purified by silica gel filtration (570 g of SiO2, toluene/EtOAc=90:10, 3 l and toluene/EtOAc=80:20 1 l). The product VII was obtained as a colorless oil (54.5 g, 81% over two steps). Rf=0.24 (SiO2, 1:1 heptane-TBME); HPLC: 87% de (Chiralcel OD, n-hexane/i-PrOH=95:5, 1.0 ml/min, 30° C.) tR=10.07 min.

Provenance & Evidence