Reserpine → 6-hydroxy-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-one

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Reaction Steps

Under nitrogen, combined 2.05 g of 6-Methoxy-1,3,3-trimethyl-1,3-dihydro-indol-2-one (10.0 mmol) with 28 ml of CH2Cl2. Added 22 ml of 1.0 M boron tribromide in CH2Cl2 dropwise over 10 minutes. Stirred at room temperature for 3.5 hours. Poured over ice-H2O and filtered to give 2.32 g of beige solid. 1H NMR (400 MHz, CD3OD) δ 1.25 (6H, s), 3.13 (3H, s), 6.42 (1H, d, J=2.08 Hz), 6.45 (1H, d, J=7.9 Hz), 7.02 (1H, d, J=8.1 Hz). M/z (APCI+) 192.1 (M+1). HPLC (aqueous 200 mM ammonium acetate buffer/acetonitrile gradient, 3.0 ml/min, Hewlett Packard ODS Hypersil 5 uM, 125×4 mm column) 3.262.

Provenance & Evidence