Water → HCID 86653602, compound

Participants

Reaction Steps

A solution of methyl (4RS,6RS)-4-(azidomethyl)-6-(4-chloro-3-(trifluoromethyl)phenyl)-6-methylcyclohex-1-enecarboxylate (21 mg, 0.054 mmol) in THF (0.5 mL) was treated with water (25 μL, 1.388 mmol) followed by triphenylphosphine (15.62 mg, 0.060 mmol). The resulting mixture was stirred at rt for 21.5 h and then concentrated under vacuum to yield a residue. The residue was dissolved in dichloromethane (0.5 mL) and the resulting solution was treated with triethylamine (0.030 mL, 0.217 mmol), dmap (3.31 mg, 0.027 mmol) and acetic anhydride (10.22 μL, 0.108 mmol). The resulting mixture was stirred at rt for 2 h and then concentrated under vacuum to yield a residue. This residue was purified by column chromatography on silica gel, eluting with 60-100% ethyl acetate-hexanes, to provide methyl (4RS,6RS)-4-(acetamidomethyl)-6-(4-chloro-3-(trifluoro-methyl)phenyl)-6-methylcyclohex-1-enecarboxylate (27 mg, estimated 68% yield), which was used in the next step without further purification despite being contaminated with about 45% by weight of triphenylphosphine oxide.

Provenance & Evidence