N-CARBOBENZYLOXY-L-PROLINEMETHYLESTER

STR19 A solution of 87 g (0.33 mol) of N-benzyloxycarbonyl-S-proline methyl ester in 200 ml of absolute ether is added dropwise, while stirring and at 0° C., to a Grignard compound prepared from 28 g (1 mol) of magnesium and 171 g (1 mol) of benzyl bromide in 400 ml of absolute ether. The reaction mixture is left to stand at room temperature for 16 hours and is then hydrolyzed by addition of water. It is then acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The combined organic phases are washed with water, dried and concentrated under reduced pressure. 163 g of a yellow oil which, according to the gas chromatogram, consists of N-benzyloxycarbonyl-S-2-(dibenzyl-hydroxymethyl)-pyrrolidine to the extent of 50percent, are obtained in this manner. The yield is accordingly calculated as 59.9percent of theory.

Molecular Weight:263.29
XLogP3:1.7
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:263.11575802
Monoisotopic Mass:263.11575802
Topological Polar Surface Area:55.8
Heavy Atom Count:19
Complexity:325
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes