Benzyl chloroformate → 4(R)-Benzyloxycarbonylamino-2,3,4,5-tetrahydro-1H-2-benzazepin-3-one

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Reaction Steps

A solution of 210 mg (1.19 mmol) of 4(R)-amino-2,3,4,5-tetrahydro-1H-2-benzazepin-3-one in 5 mL of tetrahydrofuran was treated with 5 mL of 10% aqueous potassium carbonate followed by 0.20 mL (0.24 g, 1.3 mmol, 1.1 eq) of 95% benzyl chloroformate. The mixture was stirred vigorously at room temperature for 6 hours then diluted with 20 mL of ether and the mixture transferred to a separatory funnel. The lower aqueous layer was removed and washed with several portions of ether. The combined ether washes and ether layer were washed, with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and solvents removed under vacuum to give 365 mg (1.14 mmol, 96%) of the product. 1H NMR (400 MHz, CDCl3): δ3.08 (dd; 12, 16 Hz; 1H), 3.27 (dd; 7, 16 Hz; 1H), 4.06 (d, 16 Hz, 1H), 4.75 (d, 16 Hz, 1H), 5.00 (dd; 7, 12 Hz; 1H), 5.12 (s, 2H), 7.1-7.4 (m, 9H).

Provenance & Evidence