Methanol → HCID 24876273, compound

Participants

Reaction Steps

A solution of the piperidine (B5) (20 mg, 0.077 mmol) and 3-pentanone (27 mg, 0.31 mmol) in dichloromethane (2 ml) was stirred in a vial for 90 minutes and treated with titanium (IV) isopropoxide (60 μl, 0.21 mmol) for 24 hours. To the reaction mixture was added sodium borohydride (10 mg, 0.27 mmol) and stirred for 5 hours, then treated with methanol (1 ml) and acetic acid (1 drop) for 1 hour. The solvents were evaporated and the residue was dissolved in methanol (1 ml) and acidified with TFA and purified by HPLC to give the title compound no. 56. LC-MS: m/e=329.28 (M+H). Rt=1.42 min. 1H-NMR (500 MHz, DMSO-d6): 8.65 (br.s, 1H), 8.18 (d, 1H), 7.42 (d, 1H), 7.31 (t, 1H), 7.20 (t, 1H), 7.16 (d, 1H), 4.92 (m, 1H), 3.45 (m, 1H), 3.35 (m, 1H), 3.28-3.17 (m, 2H), 3.10 (m, 1H), 2.28 (m, 2H), 2.05 (m, 1H), 1.86 (s, 3H), 1.84 (m, 4H), 1.72 (t, 1H), 1.68-1.59 (m, 2H), 1.51 (m, 1H), 1.37 (m, 1H), 0.99 (t, 5H), 0.91 (t, 1H).

Provenance & Evidence