Water → 1,3,4,9-Tetrahydro-beta-carboline-2-carboxylic acid benzyl ester

Participants

Reaction Steps

To a stirred solution of 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (20.0 g, 116.2 mmole) in dry DMF (150 mL) at RT was added N-(benzyloxycarbonyloxy)succinimide (31.84 g, 127.76 mmole) and triethylamine (13.0 g, 127.76 mmole). After 12 h, the reaction contents were poured into H2O (150 mL) and extracted with EtOAc (2×200 mL). The combined organic phases were washed sequentially with H2O and brine, then were dried over Na2SO4. Concentration under reduced pressure gave a yellow oil. Purification on silica (hexanes/EtOAc, 4:1) afforded the title compound (34.48 g, 97%) as a white solid: MS (ES) m/e 307 (M+H)+.

Provenance & Evidence