Benzylamine → HCID 59130267, compound

Participants

Reaction Conditions

Reaction Steps

To a solution 1,1-dimethylethyl 7-oxabicyclo[2.2.1]hept-5-en-2-ylcarbamate (1.0 g, 4.74 mmol) in MeOH/DCM (48 mL, 1:1) at −78° C. was bubbled through O3 until the solution maintained a blue color. N2 was then bubbled through until the blue color dissipated and a solution of benzylamine (0.49 mL, 4.5 mmol) and NaBH3CN (1.19 g, 19.0 mmol) in MeOH (22 mL) was added dropwise. After gradually warming to 25° C. over 12 hr, the mixture was partitioned between 6N NaOH and DCM. The aqueous layer was back-extracted several times with DCM and the combined organic fractions were concentrated and purified by column chromatography (silica, 0-1% MeOH in DCM (1% NH4OH )) affording the title compound as a clear oil (560 mg, 37%): LC/MS (ES) m/e 319 (M+H)+.

Provenance & Evidence