Carbamic acid, [(1S)-1-formyl-2-(phenylmethoxy)ethyl]-, 1,1-dimethylethyl ester (9CI) synthesis

12synthesis methods

Product Name:Carbamic acid, [(1S)-1-formyl-2-(phenylmethoxy)ethyl]-, 1,1-dimethylethyl ester (9CI)
CAS Number:79069-54-8
Molecular formula:C15H21NO4
Molecular Weight:279.3315

79069-15-1 Synthesis

N-Boc-(S)-2-amino-3-benzyloxy-1-propanol

79069-15-1
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Carbamic acid, [(1S)-1-formyl-2-(phenylmethoxy)ethyl]-, 1,1-dimethylethyl ester (9CI)

79069-54-8
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Yield:79069-54-8 96%

Reaction Conditions:

Stage #1: N-(tert-butyloxycarbonyl)-O-benzyl-L-serinolwith Dess-Martin periodane in dichloromethane at 20; for 2 h;
Stage #2: with sodium thiosulfate in dichloromethane;

Steps:

tert-Butyl N-[(lR)-2- (benzyloxy)-l-(hydroxymethyl)ethyl]carbamate (1.2 g, 4.3 mmole) was dissolved in CH₂C1₂ (40 mL). Dess-Martin periodinane (2.4 g, 5.5 mmole) was added. The solution was stirred for 2 h at room temperature and then quenched with Na₂S₂(? and saturated bicarbonate solution. After extracting with CH₂C1₂, the organic layer was dried over MgS0₄, filtered, and concentrated by rotary evaporation. Purification by chromatography (silica, 4/1 : Hexane /EtOAc, R_{= 0.4) afforded (S)-tert-butyl l-(benzyloxy)-3-oxopropan-2-ylcarbamate as a white solid (1.1 g, 96%).

References:

WO2011/69149,2011,A2 Location in patent:Page/Page column 26

115186-34-0 Synthesis