Carbon Tetrachloride → 17-cyclopropylmethyl-7alpha-[(2S)-3,3-dimethyl-2-hydroxybutan-2-yl]-4,5alpha-epoxy-3,6-dihydroxy-6alpha,14alpha-ethanomorphinan

Participants

Reaction Conditions

Reaction Steps

To a solution of buprenorphine (1) (10.0 g, 21.58 mMol) in CCl4 (21.7 ml, 224.5 mMol) and THF (200 ml) was added at 0° C. LiAlH4 (320 ml, 1.0 M, 320 mMol) in THF. The reaction mixture was heated to 55° C. for 24 h. The resulting reaction mixture was cooled to 0° C. and the reaction was quenched by slow, portion-wise addition of Na2SO4·10H2O (103 g), followed by addition of EtOAc (400 ml). After 20 minutes agitation, the resulting slurry was filtered through the pre-packed Solka Floc-40 (18 g). The resulting wet cake was washed thoroughly with EtOAc (2×100 ml). The combined filtrate was concentrated to dryness, affording 13.5 g of crude compound 2 which was subsequently purified by column chromatography on silica gel to afford 6.03 g of compound 2 (62.2% yield) as a white solid with a purity of >99%.

Provenance & Evidence