1,2-Dichloroethane → HCID 24789154, compound

Participants

Reaction Steps

The mixture of 5-p-tolyl-bicyclo[3.1.0]hexan-2-one (100 mg, 0.535 mmol) in DCE (3 mL) and dimethylamine (2M solution in THF, 6 mL, 5.3 mmol) was treated with sodium triacetoxyborohydride (113 mg, 0.53 mmol) at room temperature. The reaction mixture was stirred for 5 h, then the reaction mixture was concentrated, diluted with saturated NaHCO3, extracted with CH2Cl2 (3×), dried over K2CO3, filtered and concentrated in vacuo. The oily crude residue was converted to HCl salt (124 mg, 91.7%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.16 (t, 1 H) 1.73-1.80 (m, 1 H) 1.90-1.95 (m, 1 H) 2.01-2.21 (m, 3 H) 2.33-2.38 (m, 1 H) 2.81 (d, 2 H) 2.91 (d, 3 H) 3.70-3.84 (m, 1 H) 7.01-7.13 (m, 4 H). 13C NMR (400 MHz, CHLOROFORM-d) d ppm 15.70 (s, 1 C) 21.20 (s, 1 C) 24.79 (s, 1 C) 25.82 (s, 1 C) 31.66 (s, 1 C) 33.81 (s, 1 C) 43.55 (s, 1 C) 43.69 (s, 1 C) 70.51 (s, 1 C) 126.70 (s, 2C) 129.38 (s, 2C) 136.31 (s, 1C) 139.58 (s, 1 C). MS (M+1) 216.

Provenance & Evidence