Lithium borohydride → 1,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

Participants

Reaction Steps

This compound was prepared in 90% yield from the ester 4a (2.44 g, 12 mmol) by reduction with lithium borohydride in dry DME analogous to the method described earlier1,2. The product was used for the next reaction without further purification. 1H NMR (CDCl3) δ 1.14 (d, J=6.6 Hz, 3H, CHCH3), 1.44 (s, 9H, t-Bu), 2.71 (br s, 1H, CH2OH), 3.45 and 3.55 (AB part of ABX spectrum, 7 lines, JAX =4.7 Hz, JBX =7.4 Hz, JAB =10.1 Hz, 2H, 2H, CH2OH), 3.47-3.95 (m, 1H, CHCH3), 4.68 (br d, 1H, NH). Anal. Calcd. for C8H17NO3 : C, 54.84; H, 9,78; N, 7.99. Found: C, 54.84; H, 9.96; N, 7.96.

Provenance & Evidence