Water → tert-Butyl 3-methylidenepyrrolidine-1-carboxylate

HRID 358902Notes

Reaction equation

HRID 358902 reaction equation
CC(C)([O-])C.[K+].[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH:16]([CH2:19]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].O>O1CCCC1>[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][C:16](=[CH2:19])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 20067158tert-Butyl 3-((tosyloxy)methyl)pyrrolidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 15297967tert-Butyl 3-methylidenepyrrolidine-1-carboxylateYield 43.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.24 g (0.02 mole) of potassium t-butoxide were added to a solution of 3.55 g (0.01 mole) of 1-t-butoxycarbonyl-3-(p-toluenesulfonyloxymethyl)pyrrolidine [prepared as described in Step (3) above] dissolved in 50 ml of tetrahydrofuran. The mixture was then stirred at room temperature for 3 hours, after which it was poured into water and then extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried and concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through silica gel eluted with a 5:95 by volume mixture of ethyl acetate and toluene, to give 0.79 g of 1-t-butoxycarbonyl-3-methylenepyrrolidine as a pale yellow liquid.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed with water
  4. customdried
  5. concentrationconcentrated by evaporation under reduced pressure
  6. washeluted with a 5:95 by volume mixture of ethyl acetate and toluene

Sources & evidence

ORD record
ord-12d7f5139a684275b89d8c6b165a3f2b
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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