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

HRID 620147Notes

Reaction equation

HRID 620147 reaction equation
C[O:2][C:3](=O)[C@H:4]([CH3:13])[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[BH4-].[Li+]>COCCOC>[C:9]([O:8][C:6]([NH:5][C@H:4]([CH2:3][OH:2])[CH3:13])=[O:7])([CH3:11])([CH3:12])[CH3:10]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 10856577Boc-L-alanine methyl ester

Product 1

HCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamateYield 90%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

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.

Workup

  1. customThe product was used for the next reaction without further purification

Sources & evidence

ORD record
ord-5d8386a83ef24d8b80e04ce2ec1345f3
Source dataset
uspto-grants-1989_04
Patent number
US04820712

Reaction notes

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