Nitrogen → 3-chloro-N-[3-(hydroxymethyl)-1-adamantyl]benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-[(3-chlorobenzoyl)amino]adamantane-1-carboxylate (220 mg, 0.63 mmol) in THF (15 mL) at 0° C. was added LiBH4 (2.0M in THF, 0.6 mL, 1.2 mmol) dropwise under N2. After stirring at 0° C. for 30 min, the reaction mixture was allowed to warm up to room temperature overnight. The reaction was quenched with Sat. NH4Cl, and the aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 200 mg (99%) of the title compound, 3-chloro-N-[3-(hydroxymethyl)-1-adamantyl]benzamide, as a colorless oil, which was used in the next step without further purification. ESI-MS m/z: 320 (M+H)+.

Provenance & Evidence