ChemicalBook CAS DataBase List N-BOC-TRANS-4-CYANO-L-PROLINE METHYL ESTER

N-BOC-TRANS-4-CYANO-L-PROLINE METHYL ESTER synthesis

12synthesis methods

Product Name:N-BOC-TRANS-4-CYANO-L-PROLINE METHYL ESTER
CAS Number:194163-91-2
Molecular formula:C12H18N2O4
Molecular Weight:254.28

(2S, 4R)-BOC-GAMMA-MSO-PROLINE METHYL ESTER

84520-67-2
58 suppliers
$14.00/250mg

N-BOC-TRANS-4-CYANO-L-PROLINE METHYL ESTER

194163-91-2
41 suppliers
$323.00/250mg

Yield:194163-91-2 205 mg (11%)

Reaction Conditions:

in dimethyl sulfoxide;

Steps:

B Step B

Step B (4R)-1-(tert-Butyloxycarbonyl)-4-cyano-L-Proline Methyl Ester A mixture of (4R)-1-(tert-butyloxycarbonyl)-4-(methane-sulfonyloxy)-L-proline methyl ester (2.31 g, 7.14 mmol) and sodium cyanide (3.5 g, 71.4 mmol) in dry dimethylsulfoxide (46 mL) was stirred for 24 hours at 55° C. under a nitrogen atmosphere. The cooled reaction mixture was diluted with ethyl acetate, washed with water (2*), saturated brine solution, dried (MgSO₄), and evaporated. The crude product mixture was subjected to flash silica gel chromatography eluding with 15% acetone/hexane. Fractions containing the desired nitrile were combined and evaporated to afford a colorless oil; yield 205 mg (11%).

References:

US5821261,1998,A

773837-37-9 Synthesis