Hydrochloric Acid → HCID 57842645, compound

Participants

Reaction Conditions

Reaction Steps

Borane (1M solution in THF, 10 mL, 10 mmol) was added slowly dropwise to a solution of 16C (0.98 g, 4.37 mmol) in THF (60 mL) at 0° C. The reaction mixture was then heated to 70° C. overnight. The reaction mixture was cooled in an ice bath and quenched by cautious addition of hydrochloric acid (2N, 12 mL, 24 mmol). The reaction mixture was refluxed for 2 h and then concentrated almost to dryness in vacuo. The residue was coevaporated with methanol (3×), diluted with ethyl acetate and sodium hydroxide solution (2N). The aqueous layer was extracted with ethyl acetate (3×), dried (MgSO4), and concentrated in vacuo to give 16D (1.03 g, 100%) as a clear oil. MS (ESI) m/z 211.1 (M+H)+.

Provenance & Evidence