Water → tert-Butyl 3-((tosyloxy)methyl)pyrrolidine-1-carboxylate

HRID 358901Notes

Reaction equation

HRID 358901 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][CH:21]([CH2:24][OH:25])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].O>N1C=CC=CC=1>[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][CH:21]([CH2:24][O:25][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 5237175tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 20067158tert-Butyl 3-((tosyloxy)methyl)pyrrolidine-1-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

30.0 g (0.157 mole) of p-toluenesulfonyl chloride were added to a solution of 29.5 g (0.143 mole) of 1-t-butoxycarbonyl-3-hydroxymethylpyrrolidine [prepared as described in Step (2) above] dissolved in 500 ml of pyridine. The mixture was then stirred for 5 hours whilst ice-cooling, after which it was stirred at room temperature overnight. The reaction mixture was poured into 1 liter of water and then extracted with ethyl acetate. The extract was washed with water, dried and concentrated under by evaporation reduced pressure. The residue was subjected to column chromatography through silica gel eluted with a 1:4 by volume mixture of ethyl acetate and toluene, to give 36.6 g of 1-t-butoxycarbonyl-3-(p-toluenesulfonyloxymethyl)pyrrolidine as a pale brown oil, which gradually crystallized.

Workup

  1. temperaturecooling
  2. stirringafter which it was stirred at room temperature overnight
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated under by evaporation reduced pressure
  7. washeluted with a 1:4 by volume mixture of ethyl acetate and toluene

Sources & evidence

ORD record
ord-3fdd1c4a913a434fb4fc8e7acf9c1f91
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

Loading…