Aluminium lithium hydride → HCID 59438412, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 126 mg (3.15 mmol) LiAlH4 in THF (2.7 ml) at temperature below 10° C. was added dropwise a solution of 530 mg (1.576 mmol) rac-3-azido-3-phenyl-piperidine-1-carboxylic acid benzyl ester in THF (5.3 ml). The ice bath was removed. The temperature rose to 35° C. The mixture was then heated in a 65° C. oil bath for 1 hour. The mixture was cooled to 0° C. Water (125 ul), NaOH 5N (125 ul) and finally water (0.375 ml) were added dropwise maintaining the temperature below 10° C. The mixture was diluted with ethyl acetate. Sodium sulfate was added. The mixture was filtered and the filtrate was concentrated in vacuo. The crude oil was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%) to provide 0.14 g (47%) of the title compound as a yellow oil. MS (m/e): 191.5 (M+H+)

Provenance & Evidence