Water → 2-Phenylprolinol

Participants

Reaction Conditions

Reaction Steps

Lithium aluminium hydride (1M in tetrahydrofuran; 10.6 ml) was added to a cooled (0° C.) suspension of (±)-2-phenylproline hydrochloride (0.85 g) and the mixture heated at reflux for 1.5 h. After cooling to 0° C., water (1 ml) was added followed by 2M NaOH (1 ml) and water (2 ml). The reaction mixture was diluted with ethyl acetate (50 ml) then filtered through a pad of Hi-flo and the residue concentrated in vacuo to give (±)-2-phenylprolinol as a yellow oil which solidified on standing. 1H NMR (250 MHz, CDCl3) d 7.42-7.20 (5H, m, ArH), 3.60 (1H, d, J=10.0 Hz, CHHOH), 3.49 (1H, d, J=10.0 Hz, CHHOH), 3.07 (2H, t, J=5.7 Hz, CH2N), 2.43 (2H, br s, OH and NH), 2.19-1.75 (4H, m).

Provenance & Evidence