ChemicalBook CAS DataBase List N-Boc-Trans-4-Hydroxy-D-proline methyl ester

N-Boc-Trans-4-Hydroxy-D-proline methyl ester synthesis

13synthesis methods

Product Name:N-Boc-Trans-4-Hydroxy-D-proline methyl ester
CAS Number:135042-17-0
Molecular formula:C11H19NO5
Molecular Weight:245.27

481704-21-6 Synthesis

(2S,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride

481704-21-6
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$11.00/250mg

24424-99-5 Synthesis

24424-99-5
823 suppliers
$13.50/25G

N-Boc-Trans-4-Hydroxy-D-proline methyl ester

135042-17-0
161 suppliers
$8.00/250mg

Yield:135042-17-0 100%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in 1,4-dioxane at 0 - 20; for 1 h;

Steps:

7

Add di-tert-butyl dicarbonate (11.2 g, 51.35 mmol) to a solution of 4-(S)- hydroxypyrrolidine-2- (R)-carboxylic acid methyl ester hydrochloride (7.17 g, 39.5 mmol) in 1,4-dioxane (80 mL). Cool in an ice bath and add N,N-diisopropylethylamine (11.7 mL, 67.2 mmol). Remove ice bath and stir 1 h at room temperature. Concentrate and dissolve in ethyl acetate, wash with 5% aqueous citric acid solution (2 x100 mL), water, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with hexanes and ethyl acetate) to give the title compound as a white solid (9.83 g, 100%). MS (ES): m/z = 246.1 [M+H].

References:

WO2005/108358,2005,A2 Location in patent:Page/Page column 38-39