N-BOC-(2S,3S)-2-AMINO-3-BENZYLOXY-1-BUTANOL synthesis

4synthesis methods

Product Name:N-BOC-(2S,3S)-2-AMINO-3-BENZYLOXY-1-BUTANOL
CAS Number:79069-63-9
Molecular formula:C16H25NO4
Molecular Weight:295.37

15260-10-3
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N-BOC-(2S,3S)-2-AMINO-3-BENZYLOXY-1-BUTANOL

79069-63-9
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Yield:79069-63-9 84%

Reaction Conditions:

Stage #1: N-Boc-O-benzyl-L-threoninewith 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide;N-ethyl-N,N-diisopropylamine in ethyl acetate at 0; for 0.166667 h;
Stage #2: with sodium tetrahydroborate in water;ethyl acetate at 0; for 0.583333 h;

Steps:

General procedure for the reduction of carboxylic acids to alcohols using T3P-NaBH₄:

General procedure: To a solution of carboxylic acid (10 mmol) in THF (10 mL), DIPEA (11 mmol, 1.42 mL) and 50% T3P in EtOAc (20 mmol, 6.36 mL) were added at 0 °C and the solution was stirred for about 10 min. Then aqueous solution of NaBH₄ (10 mmol, 388 mg in 0.3 mL of H₂O) was added to the reaction mixture at the same temperature and the reaction was allowed to stir till the completion of the reaction as indicated by TLC. After the completion of the reaction, the solvent was evaporated and the crude alcohol was extracted into EtOAc and the organic phase was washed with 5% citric acid (10 mL × 2), 5% Na₂CO₃ (10 mL × 2), water, and brine solution. The product was isolated after the evaporation of solvent under reduced pressure and dried over anhydrous Na₂SO₄.

References:

Nagendra;Madhu;Vishwanatha;Sureshbabu, Vommina V. [Tetrahedron Letters,2012,vol. 53,# 38,p. 5059 - 5063] Location in patent:experimental part