(R,S)-Boc-2-amino-tetradecanoic acid → Tert-butyl n-[1-(r/s)-(hydroxymethyl)tridecyl]carbamate

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Reaction Steps

2-(R/S)-[(tert-butoxycarbonyl)amino]tetradecanoic acid 41 (1.00 g, 2.92 mmol) in abs. THF (3 ml) was added slowly dropwise to BH3-THF complex (1.0M, 5.8 ml, 5.80 mmol) at 0° C. After stirring for 2 hours, the reaction mixture was quenched with 10% acetic acid in methanol (v/v) and evaporated. The residue was taken up in CH2Cl2 (10 ml) and washed with 1M KHSO4(aq) (1×20 ml) and brine (2×20 ml). The solution was then dried over MgSO4, filtered and evaporated. Purification by column chromatography gave 44 (821 mg, 86%).

Provenance & Evidence