Hydrochloric Acid → HCID 136216249, compound

Participants

Reaction Steps

To a solution of 4-(4-chloro-2-methyl-phenyl)-3-cyclopropyl-1,6,6-trimethyl-4,8-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one (1.2 g, 3.19 mmol) in THF (20 mL) was added a solution of borane tetrahydro-furan complex (14 mL, 1M in THF, 4 mmol, Acros) at about 4° C. Subsequently, the mixture was stirred for about 18 h at rt. After cooling to about 4° C., HCl (5 M aqueous, 12 mL) was added dropwise and the mixture was stirred for about 2 h at about 4° C., then NaOH (1 M aq, 60 mL) and ethyl acetate (200 mL) were added. The layers were separated and the aqueous layer was extracted with ethyl acetate (50 mL). The combined organic layers were washed with water (2×25 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, ethyl acetate/hexanes 1:1 to 100:0) to give 4-(4-chloro-2-methyl-phenyl)-3-cyclopropyl-1,6,6-trimethyl-7,8-dihydro-4H-pyrazolo[3,4-e][1,4]thiazepine as white solid (0.75 g, 2.1 mmol, 65%). LC-MS (Table 1, Method e) Rt=7.48 min, m/z: 362 (M+H)+; 1H-NMR (CDCl3, Bruker 400 MHz) δ 0.38-0.65 (4H, m) 0.91-0.99 (1H, m) 1.01 (3H, s) 1.35 (3H, s) 2.52 (3H, s) 3.09 (1H, dd, J=14.5, 5.5 Hz) 3.40 (1H, dd, J=14.5, 5.0 Hz) 3.62 (3H, s) 3.65 (1H br.t.) 5.17 (1H, s) 7.07 (1H, dd, J=8.5, 2.0 Hz) 7.16 (1H, d, J=2.0 Hz) 7.21 (1H, d, J=8.5 Hz).

Provenance & Evidence