ChemicalBook CAS DataBase List N-BOC-4,4-difluoro-L-proline

N-BOC-4,4-difluoro-L-proline synthesis

8synthesis methods

Product Name:N-BOC-4,4-difluoro-L-proline
CAS Number:203866-15-3
Molecular formula:C10H15F2NO4
Molecular Weight:251.23

203866-17-5 Synthesis

N-Boc-4,4-difluoro-L-proline methyl ester

203866-17-5
137 suppliers
$13.00/100mg

203866-15-3
175 suppliers
$15.00/250mg

Yield:203866-15-3 99%

Reaction Conditions:

Stage #1: 1-tert-butyl 2-methyl (2S)-4,4-difluoropyrrolidine-1,2-dicarboxylatewith water;sodium hydroxide in tetrahydrofuran;methanol at 20; for 1 h;
Stage #2: with hydrogenchloride in water;

Steps:

63

PREPARATION 63CS^-l -iiert-ButoxycarbonylJ^^-difluoropyrrolidine^-carboxylic acid1.08 g (4.08 mmol) of (S)^ -ferf-butyl 2-methyl 4,4-difluoropyrrolidine-1 ,2-dicarboxylate (purchased from Aldrich; cat. no. 702463) were dissolved in a mixture of 10 mL of methanol and 10 mL of tetrahydrofurane and 6.12 mL of a 2M aqueous solution of sodium hydroxide were added. The solution was stirred at room temperature for 1 hour and then the organic solvents were removed. The remaining solution was diluted with water and 6.12 mL of 2M hydrochloric acid were added. The product that precipitated was extracted with dichloromethane (x3), the combined organic layers were washed with brine, dried over magnesium sulphate, filtered and the solvent was removed. 1 .01 g (99% yield) of the title compound were obtained as a white solid.LRMS (m/z): 250 (M-1 )⁺.

References:

WO2012/146666,2012,A1 Location in patent:Page/Page column 138-139

102195-80-2 Synthesis