Lithium hydroxide, monohydrate → 1,2-Pyrrolidinedicarboxylic acid, 4,4-diMethyl-, 1-(1,1-diMethylethyl) ester, (2R)-
Reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:4]([C:14]([O:16]CC2C=CC=CC=2)=[O:15])[CH2:3]1.O[Li].O>O1CCOCC1.O>[C:10]([O:9][C:7]([N:5]1[CH2:6][C:2]([CH3:24])([CH3:1])[CH2:3][C@@H:4]1[C:14]([OH:16])=[O:15])=[O:8])([CH3:13])([CH3:11])[CH3:12]Participants
4
Procedure
To a mixture of (R)-2-benzyl 1-tert-butyl 4,4-dimethylpyrrolidine-1,2-dicarboxylate (D40) (198 mg, 0.59 mmol) in dioxan/water (4/4 ml), LiOH.H2O (100 mg, 2.37 mmol) was added and the mixture was left stirring at RT for 18 hrs. Organic solvent was evaporated off and the reaction mixture was diluted with water (8 ml), washed with Et2O (2×10 ml), acidified with acetic acid to pH˜4-5 and extracted with Et2O (3×10 ml). The organic phases were collected, dried over Na2SO4 and evaporated in vacuo to afford the title compound (D41) (84 mg).