Acetic Acid → HCID 136216213, compound

Participants

Reaction Steps

A mixture of 4-(4-bromo-2-methyl-phenyl)-1,7-dimethyl-3-(2-pyridyl)-4,6-dihydropyrazolo[3,4-e][1,4]thiazepine (0.48 g, 1.13 mmol., Preparation J.1), acetic acid (0.194 mL, 3.40 mmol) and Na(AcO)3BH (0.29 g, 1.36 mmol) in DCE (30 mL) was stirred at rt for about 16 h. Additional acetic acid (0.194 mL, 3.4 mmol) and Na(AcO)3BH (0.29 g, 1.36 mmol) were added and stirring was continued for about another 24 h, at rt. The resulting mixture was concentrated in vacuo and partitioned between 5% aq sodium bicarbonate (60 mL) and ethyl acetate (35 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (35 mL). The combined organic layers were washed with water (20 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, ethyl acetate/hexanes 1:1) to give 4-(4-bromo-2-methyl-phenyl)-1,7-dimethyl-3-(2-pyridyl)-4,6,7,8-tetrahydropyrazolo[3,4-e][1,4]thiazepine (0.413 g, 0.96 mmol, 85%) as a pale yellow oil as a racemic mixture of two diastereomers (ratio 63:37). LC-MS (Table 1, Method g) Rt=2.75 and 2.79 min; m/z 429, 431 (M+H)+

Provenance & Evidence