Sodium Hydroxide → HCID 22036736, compound

Participants

Reaction Conditions

Reaction Steps

7-fluoro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (76 mg, 0.38 mmol) dissolved in toluene (1 mL) and cooled to 0° C. in an ice bath. Red-Al (275 mL, 0.91mmol) was added and then the reaction allowed to warm to room temperature. The reaction was heated at reflux for 1.5 hours. 1 N sodium hydoxide was added slowly until pH>10, this was stirred for 10 minutes, extracted with dichloromethane (3×25 mL), washed with water, and dried (sodium sulfate). The concentrated organics were purified by preparative thin layer chromatography on silica gel and eluted with 50% ethyl acetate in hexanes to give 7-fluoro-2,3,4,5-tetrahydro-1,5-benzothiazepine (30.8 mg, 93%). 1H NMR (CDCl3, 300 MHz): δ 7.32 (t, 1H, J=7.5 Hz), 6.53-6.42 (m, 2H), 4.09 (s-broad, 1H), 3.31-3.27 (m, 2H), 2.83-2.79 (m, 2H), 2.11-2.04 (m, 2H) ppm.

Provenance & Evidence