(4S)-2,8-Dimethyl-4-[(toluenesulfonyl)amino]-5-nonanone → (4S)-2,8-Dimethyl-5-hydroxy-4-[(toluenesulfonyl)amino]-5-vinylnonane

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Reaction Steps

To a stirred 0° C. solution of the resultant compound of Example 37 (79 mg, 0.23 mmol) in dry THF (8 ml) was added vinyl magnesium bromide (1.5 ml of a 1.0M solution in THF) dropwise. The mixture was warmed (room temperature, 10 hours), quenched (8 ml H2O+2 ml brine), acidified with 0.1M H3PO4 (pH=7), and extracted with ether (3×4 ml). The combined ether phase was washed (4 ml brine), dried (Na2SO4), filtered, and evaporated to give 81 mg (95%) of the desired product as a 4:1 mixture of diastereomers.

Provenance & Evidence