Aluminium lithium hydride → 2-(Boc-amino)-4-(hydroxymethyl)pyridine

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Reaction Steps

A solution of to 2-[N,N-bis(tert-Butoxycarbonyl)amino]-isonicotinic acid ethyl ester (35.0 g, 95.5 mmol) in THF (350 mL) was treated with LiAlH4 (7.25 g, 191 mmol) and refluxed for 1 h under nitrogen. The reaction mixture was poured carefully onto crushed ice and the product extracted several times with CHCl3 and CHCl3: MeOH (9:1). The combined organic extracts were dried, filtered and concentrated under reduced pressure to give (4-hydroxymethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (18.5 g, 86%) as a pale yellow solid.

Provenance & Evidence