Benzyl (4R)-1-Boc-4-hydroxy-D-prolinate synthesis

6synthesis methods

Product Name:Benzyl (4R)-1-Boc-4-hydroxy-D-prolinate
CAS Number:132622-92-5
Molecular formula:C17H23NO5
Molecular Weight:321.37

100-39-0
423 suppliers
$10.00/10g

(2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid

135042-12-5
186 suppliers
$6.00/1g

132622-92-5
10 suppliers
inquiry

Yield:132622-92-5 100%

Reaction Conditions:

Stage #1: (4R)-1-(tert-butoxycarbonyl)-4-hydroxy-D-prolinewith caesium carbonate in methanol;water at 0; for 0.5 h;
Stage #2: benzyl bromide in N,N-dimethyl acetamide at 20;

Steps:

14.2 2-benzyl 1-tert-butyl (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

At room temperature,15a (8.6 g, 37.21 mmol) was dissolved in methanol (80 mL), cooled to 0 ° C,A solution of cesium carbonate (6.06 g, 18.61 mmol) in water (42 mL) was added dropwise to the reaction solution,Stirred for 30 minutes and concentrated under reduced pressure to remove the solvent to give a white solid.The residue was dissolved in N, N-dimethylformamide (68 mL), benzyl bromide (6.36 g, 37.21 mmol) was added and the reaction was stirred at room temperature overnight.Most of the solvent was removed by distillation under reduced pressure, water (100 mL) was added, and extracted with ethyl acetate (100 mL x 3).The organic phases were combined and washed successively with water (100 mL x 1), saturated brine solution (100 mL x 2).Dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give a pale yellow liquid 15b (11.95 g, yield 100%).

References:

TW2017/8221,2017,A Location in patent:Page/Page column 92; 93; 94

24424-99-5 Synthesis