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

HRID 1278075Notes

Reaction equation

HRID 1278075 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

5

Reactant 3

HCID 10340Sodium CarbonateHCID 62493Pivaloyl chlorideHCID 234525183-[(1-Methylpyrrolidin-2-yl)methyl]phenol

Product 1

HCID 234525021-Methyl-2-(3-pivaloyloxybenzyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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.

Workup

  1. additionPour
  2. extractionbefore extracting it with diethyl ether
  3. dry with materialDry the ether
  4. extractionextract over sodium sulfate
  5. customdistil off the solvent
  6. customdistil the residue under a high vacuum

Sources & evidence

ORD record
ord-d88f10b164c4414fbb70caf3c5365c1d
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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