Acetic Acid → HCID 24904639, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of pyrrolidin-3-ol (3.8 g, 44 mmol) and 3-methoxybenzaldehyde (5.0 g, 37 mmol) in 1,2-dichloroethane (100 mL), was added sodium triacetoxyborohydride (15.5 g, 73 mmol) portionwise at 0° C. Acetic acid (2.8 mL, 44 mmol) was subsequently added. The reaction mixture was warmed to 45° C. and stirred overnight. A saturated solution of sodium bicarbonate was added and the resulting mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product, 1-(3-methoxybenzyl)pyrrolidin-3-ol, obtained (6.0 g, 79%) as a yellow oil, was used as such in the next reaction: 1H NMR (CDCl3, 400 MHz) δ 7.28-7.18 (m, 1H), 6.92-6.86 (m, 2H), 6.82-6.76 (m, 1H), 4.32 (tdd, J=2.3, 5.0, 7.3 Hz, 1H), 3.83-3.78 (m, 3H), 3.59 (s, 2H), 2.86 (dt, J=4.9, 8.6 Hz, 1H), 2.68 (d, J=9.8 Hz, 1H), 2.53 (dd, J=5.3, 10.3 Hz, 1H), 2.45 (br s, 1H), 2.30 (dt, J=6.5, 8.9 Hz, 1H), 2.24-2.13 (m, 1H), 1.78-1.68 (m, 1H); ESI MS (m/z) 208 [M+H]+.

Provenance & Evidence