Benzyl chloroformate → Benzyl 7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-ylcarbamate

Participants

Reaction Steps

A solution of benzyl chloroformate (5.84 mL, 41.1 mmol) in 5 mL CH2Cl2 was added dropwise via addition funnel to Example 24A (3.05 g, 18.7 mmol) and Hunig's base (8.14 mL, 46.7 mmol) in dichloromethane (55 mL) at ambient temperature. After 18 hr IN (aq) NaOH solution (50 mL) was added and the reaction was stirred vigorously for 15 min. The separated organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was triturated with diethyl ether and the solid collected by suction filtration. The result was 3.37 g (61% yield) of the title compound as a brown solid. 1H NMR (300 MHz, DMSO-d6) δ 8.82 (s, 1H), 7.30-7.45 (m, 5H), 7.14 (m, 1H), 7.05 (t, 1H), 6.90 (m, 1H), 5.12, (s, 2H), 4.77 (d, 1H), 3.87 (m, 1H), 2.86 (m, 2H), 2.71 (m, 1H), 2.43 (m, 1H), 1.84 (m, 1H), 1.58 (m, 1H). MS (APCI+) m/z 298 (M+H)+.

Provenance & Evidence