Benzyl chloroformate → HCID 15487827, compound

Participants

Reaction Steps

To a mixture of (3S)-1,2,3,4-tetrahydro-7-hydroxy-isoquinoline-3-carboxylic acid (1.00 g, 5.18 mmol), sodium bicarbonate(0.88 g, 10.5 mmol), tetrahydrofuran (30 mL), and water (30 mL) was added benzyl chloroformate (0.84 mL, 5.88 mmol) at room temperature. The mixture was stirred overnight and concentrated to about 10 mL. The residue was acidified with 20% HCl until pH ˜4. The white solid formed was filtered and washed with water, and the filtrate was extracted with dichloromethane (×3). The organic layer was dried, concentrated, and combined with the white solid from filtration. To a solution of this compound (1.85 g, 5.66 mmol) in methanol (15 mL) and benzene (10 mL) at 4° C. was added 2.0 M (trimethylsilyl)diazomethane (4.2 mL, 8.4 mmol) in hexane. After 2 hours at 4° C., the solution was concentrated to give the title compound as a yellow oil (1.99 g, 100%). 1H NMR (CDCl3) δ 7.40-7.30 (m, 5H), 6.96 (d, 1H, J=8.1 Hz), 6.67-6.64 (m, 1H), 6.57 (d, 1H, J=14.3 Hz), 5.25-5.11 (m, 3H), 4.68 (d, 1H, J=14.9 Hz), 4.55-4.45 (m, 1H), 3.60 (s, 1.5 14), 3.52 (s, 1.5H), 3.19-3.06 (m, 2H).

Provenance & Evidence