Methanol → HCID 69880756, compound

Participants

Reaction Conditions

Reaction Steps

To a −78° C. solution of N-(4-methoxycarbonylphenyl) pyrid-3-ylmethylamine (105 g, 0.433 moles, leg) in THF (17 volumes) was added slowly DIBAl-H (1M in toluene, 1084 mL, 1.084 moles, 2.5 eq,) and held cold for 1 hour. The reaction was then allowed to warm to 0° C. for 2 h. The reaction was carefully quenched with methanol (1.8 eq). It was then diluted with ether (62 volumes) and Saturated Rochelle's salt (37 volumes) and stirred vigorously overnight. The layers were separated and the aqueous extracted with EtOAc. The combined organics were washed with brine, dried with MgSO4, filtered, and concentrated to give N-(4-hydroxymethylphenyl)pyrid-3-ylmethylamine (88.2 g, 95% Yield).

Provenance & Evidence