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ChemicalBook CAS DataBase List N-Boc-Trans-4-Hydroxy-D-proline methyl ester
135042-17-0

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

13synthesis methods
481704-21-6 Synthesis
(2S,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride

481704-21-6
119 suppliers
$11.00/250mg

24424-99-5 Synthesis
Di-tert-butyl dicarbonate

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

-

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

24424-99-5 Synthesis
Di-tert-butyl dicarbonate

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

178962-09-9 Synthesis
D-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI)

178962-09-9
33 suppliers
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