ChemicalBook CAS DataBase List TERT-BUTYL (2R,4S)-4-FLUORO-2-(HYDROXYMETHYL)PYRROLIDINE-1-CARBOXYLATE

TERT-BUTYL (2R,4S)-4-FLUORO-2-(HYDROXYMETHYL)PYRROLIDINE-1-CARBOXYLATE synthesis

5synthesis methods

Product Name:TERT-BUTYL (2R,4S)-4-FLUORO-2-(HYDROXYMETHYL)PYRROLIDINE-1-CARBOXYLATE
CAS Number:869527-46-8
Molecular formula:C10H18FNO3
Molecular Weight:219.25

Methyl (2R,4S)-1-Boc-4-fluoropyrrolidine-2-carboxylate

647857-39-4
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TERT-BUTYL (2R,4S)-4-FLUORO-2-(HYDROXYMETHYL)PYRROLIDINE-1-CARBOXYLATE

869527-46-8
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Yield:869527-46-8 100%

Reaction Conditions:

Stage #1: 1-(tert-butyl) 2-methyl (2R,4S)-4-fluoropyrrolidine-1,2-dicarboxylatewith lithium borohydride in tetrahydrofuran at 0 - 20; for 18 h;
Stage #2: with acetic acid in tetrahydrofuran;water at 0;

Steps:

4

Add lithium borohydride (0.43 g, 19.6 mmol) to an ice cold solution of 4- (S)- fluoropyrrolidine-N1,2-(R)-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (3.9 g, 13.08 mmol) in THF (50 mL). Warm'to room temperature over 18 h. Cool in ice bath. Slowly add acetic acid (3 mL) and water and extract with ethyl acetate. Wash extract with water, saturated aqueous sodium bicarbonate solution, 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 thick oil (2.90 g, 100%). MS (ES) : m/z = 218.2 [M+H].

References:

WO2005/108358,2005,A2 Location in patent:Page/Page column 36

681128-50-7 Synthesis