Sodium Carbonate → 1-Methyl-2-(3-pivaloyloxybenzyl)pyrrolidine

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][N:7]1[CH3:11].[C:15](Cl)(=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1>[CH3:11][N:7]1[CH2:8][CH2:9][CH2:10][CH:6]1[CH2:5][C:4]1[CH:12]=[CH:13][CH:14]=[C:2]([O:1][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH:3]=1

Participants

Procedure

Stir 380 mg of 2-(3-hydroxybenzyl)-1-methylpyrrolidine at 100° for 2.5 hours with 480 mg of pivaloyl chloride in 5 ml of absolute pyridine. Pour the resulting reaction mixture into 50 ml of ice water. Then add 20 ml of saturated sodium carbonate solution thereto before extracting it with diethyl ether. Dry the ether extract over sodium sulfate, distil off the solvent and distil the residue under a high vacuum to obtain 320 mg (58% of theory) of the title compound as colorless liquid of b.p. 95° to 100° at 0.002 mm of Hg.