Aluminium lithium hydride → HCID 86705562, compound

Participants

Reaction Steps

To a stirred mixture of 384 (7.1 g, 20.6 mmol) in THF (150 mL) at −78° C. was added dropwise 1M LiAlH4 (30.8 mL, 30.8 mmol) and stirring was continued for 3 to 4 h. The mixture was diluted with THF, quenched by portion-wise addition of Na2SO4 decahydrate and filtered. Solids were rinsed with additional THF, and the filtrate concentrated. The crude product was purified by SiO2 chromatography eluting with 50% EtOAc/hexanes to afford 3.58 g (55%) of (R)-tert-butyl 1-(4-(difluoromethoxy)phenyl)-3-hydroxypropylcarbamate (386) as a clear viscous liquid which was ca. 95% ee by chiral HPLC.

Provenance & Evidence