HCID 14304675, compound → HCID 14304678, compound

Participants

Reaction Steps

To a stirred and ice-cooled suspension of lithium aluminum hydride (0.51 g) in dry tetrahydrofuran (20 ml), was added dropwise a solution of methyl (S)-3-(3,4,6,7,8,9-hexahydro-3-oxo-2H-naphtho[2,3-b][1,4]oxazin-2-yl)propionate (1.75 g) in dry tetrahydrofuran (10 ml). The whole was stirred at 0° C. for 1.5 hour and quenched with water. After neutralization with 4N-HCl, the insoluble material was filtered off. The filtrate was extracted with ethyl acetate, and the ethyl acetate layer was washed with water and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (60 g) with ethyl acetate-hexane (3:1, v/v) to yield (S)-6,7,8,9-tetrahydro-2-(3-hydroxypropyl)-2H-naphtho[2,3-b][1,4]oxazin-3(4H)-one as colorless needles (1.56 g, 98.7%), m.p. 139°-140° C. [α]D26 +1.4° (c=0.5, CHCl3).

Provenance & Evidence