ChemicalBook CAS DataBase List tert-Butyl (2R,4R)-4-[(tert-Butyldimethylsilyl)oxy]-2-(hydroxymethyl)pyrrolidine-1-carboxylate, cis

tert-Butyl (2R,4R)-4-[(tert-Butyldimethylsilyl)oxy]-2-(hydroxymethyl)pyrrolidine-1-carboxylate, cis synthesis

11synthesis methods

Product Name:tert-Butyl (2R,4R)-4-[(tert-Butyldimethylsilyl)oxy]-2-(hydroxymethyl)pyrrolidine-1-carboxylate, cis
CAS Number:114676-58-3
Molecular formula:C16H33NO4Si
Molecular Weight:331.52

114760-51-9 Synthesis

1,2-Pyrrolidinedicarboxylic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2R,4R)-

114760-51-9
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tert-Butyl (2R,4R)-4-[(tert-Butyldimethylsilyl)oxy]-2-(hydroxymethyl)pyrrolidine-1-carboxylate, cis

114676-58-3
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Yield:114676-58-3 100%

Reaction Conditions:

with lithium borohydride in tetrahydrofuran at 0 - 20; for 16 h;

Steps:

2 tert-butyl (2R,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

5A (71.9 g, 0.2 mol) was dissolved in tetrahydrofuran (300 mL) at room temperature, cooled to 0 ° C,Lithium borohydride (10.6 g, 0.49 mol) was added in portions and the reaction was allowed to proceed to room temperature for 16 hours.The reaction solution was cooled to 0 ° C, ammonium chloride solution (100 mL) was added, and the pH was adjusted to 7 with hydrochloric acid (3 mol / L, 30 mL).The organic phase was extracted with ethyl acetate (40 mL x 3) and washed successively with sodium bicarbonate solution (150 mL x 1), saturated brine solution (150 mL x 2).Dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give colorless liquid 5B (67.0 g, yield 100%).

References:

TW2017/8221,2017,A Location in patent:Page/Page column 49; 50