Iodine → HCID 24904639, compound

Participants

Reaction Conditions

Reaction Steps

To pyrrolidin-3-ol (3.4 g, 39 mmol) in methanol (150 mL) was added 3-methoxybenzaldehyde (6.4 g, 47 mmol) and iodine (0.40 g, 32 mmol). After stirring for 5 h, the reaction mixture was cooled to 0° C. and sodium borohydride (2.9 g, 78 mmol) was added portionwise. The reaction mixture was warmed to ambient temperature and stirred overnight. Water (10 mL) was added and most of the tetrahydrofuran was removed in vacuo. Additional water (25 mL) was added and the aqueous layer was extracted with methylene chloride (50 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (methylene chloride to 90:9:1 methylene chloride/methanol/ammonium hydroxide) to provide 1-(3-methoxybenzyl)pyrrolidin-3-ol (2.0 g, 25%) as a yellow oil: 1H NMR (DMSO-d6, 300 MHz) δ 7.21 (dd, J=8.1, 8.1 Hz, 1H), 6.87-6.77 (m, 3H), 4.66 (d, J=4.5 Hz, 1H), 4.21-4.14 (m, 1H), 3.73 (s, 3H), 3.56-3.45 (m, 2H), 2.64 (dd, J=9.6, 6.3 Hz, 1H), 2.58-2.49 (m, 1H), 2.43-2.34 (m, 1H), 2.28 (dd, J=9.6, 7.5 Hz, 1H), 2.04-1.92 (m, 1H), 1.57-1.51 (m, 1H).

Provenance & Evidence