4-(tert-Butoxycarbonyl)morpholine-3-carboxylic acid → Tert-butyl 3-(hydroxymethyl)morpholine-4-carboxylate

Participants

Reaction Steps

A 1M solution of borane-tetrahydrofuran complex in THF (8.65 mL; 8.65 mmol; 2 eq.) was added to a cold (0° C.) solution of morpholine-3,4-dicarboxylic acid 4-tert-butyl ester (1 g; 4.32 mmol; 1 eq.) in THF (10 mL) and the resulting mixture was stirred at room temperature for 1 hour. The solution was diluted with EA, washed with sat. aq. NaHCO3 then brine, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (EA/heptane) afforded the title compound (600 mg, 64%) as a colourless oil.

Provenance & Evidence