Aluminium lithium hydride → HCID 58171625, compound

Participants

Reaction Steps

To a solution of 4-(2-hydroxy-2-methylpropyl)-4-phenylpyrrolidin-2-one (crude, 2.17 g, 9.3 mmol) in anhydrous THF (40 mL) was added LiAlH4 (1.42 g, 37.3 mmol) at −10° C. in a dry-ice/acetone bath. The reaction mixture was refluxed overnight. LC-MS showed that about 90% of desired product was produced. The reaction mixture was diluted with anhydrous THF (200 mL) and filtered through Celite. The filter cake was washed several times with anhydrous THF. The filtrate was concentrated to dryness to give crude 2-methyl-1-(3-phenylpyrrolidin-3-yl)propan-2-ol (1.34 g, 67%), which was used directly for next step without purification. 1H NMR (CDCl3 400 MHz): δ 7.28-7.22 (m, 4H), 7.16-7.12 (m, 1H), 3.82 (s, br, 1H), 3.24-3.16 (m, 2H), 3.11 (m, 1H), 2.95 (m, 1H), 2.26-2.13 (m, 2H), 1.98 (s, 2H), 1.09 (s, 3H), 1.05 (s, 3H).

Provenance & Evidence