Triphosgene → HCID 123350859, compound

Participants

Reaction Steps

To a stirred solution of 3-(benzyloxy)-1-methylcyclobutanamine (64.9 mg, 0.339 mmol) in THF (10 mL) was added TEA (0.14 mL, 1.357 mmol) followed by triphosgene (100 mg, 0.339 mmol) at 0° C. After stirring for 10 min, a solution of Intermediate 185B (100 mg, 0.34 mmol) in THF (2 mL) was added at 0° C. and the resulting solution was allowed to warm to RT and stir for 16 h. The reaction mixture was quenched with a saturated aqueous solution of NH4Cl and extracted with DCM (3×20 mL). The combined organic layers were dried over Na2SO4 and evaporated to afford the crude reaction mixture which was purified by silica gel chromatography (12 g REDISEP® column, eluting with 2% MeOH in CHCl3). Fractions containing the product were combined and evaporated to afford Intermediate 260A (70 mg, 40% yield) as a pale yellow solid. MS(ES): m/z=512 [M+H]+.

Provenance & Evidence