Ethyl Acetate → (2S,4R)-1-allyloxycarbonyl-2-phthalimidomethyl-4-methanesulfonyloxypyrrolidine

HRID 1034524Notes

Reaction equation

HRID 1034524 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:9][C@H:8]1[CH2:17]OS(C1C=CC(Cl)=CC=1)(=O)=O)=[O:6])[CH:2]=[CH2:3].[C:29]1(=[O:39])[NH:33][C:32](=[O:34])[C:31]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:30]12.[K].C(OCC)(=O)C>CN(C)C=O>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:14])=[O:15])[CH2:9][C@H:8]1[CH2:17][N:33]1[C:32](=[O:34])[C:31]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:30]2[C:29]1=[O:39])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 22851791(2S,4R)-1-allyloxycarbonyl-2-p-chlorobenzenesulfonyloxy methyl-4-methanesulfonyloxypyrrolidineHCID 24194345Phthalimide potassium salt

Product 1

HCID 57022733(2S,4R)-1-allyloxycarbonyl-2-phthalimidomethyl-4-methanesulfonyloxypyrrolidineYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (2S,4R)-1-allyloxycarbonyl-2-p-chlorobenzenesulfonyloxymethyl-4-methanesulfonyloxypyrrolidine (23.7 g: ca. 50 mmole) in dimethylformamide (50 ml), potassium phthalimide (10.2 g: 55 mmole) is added in a nitrogen atmosphere, and the mixture is stirred at 60° C. for 3.5 hours. The reaction mixture is poured into a stirring mixture of ice water (500 ml) and ethyl acetate (500 ml). The organic layer is successively washed with water (4 times) and saturated brine, dried over magnesium sulfate, and concentrated in vacuo. The residue is recrystallized from a mixture of n-hexane and toluene. The solid is filtered off and the filtrate is purified by silica gel chromatography (toluene-ethyl acetate) to give crude (2S,4R)-1-allyloxycarbonyl-2-phthalimidomethyl-4-methanesulfonyloxypyrrolidine (12.41 g). Yield: 61%. Colorless oil.

Workup

  1. washThe organic layer is successively washed with water (4 times) and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue is recrystallized from a mixture of n-hexane and toluene
  5. filtrationThe solid is filtered off
  6. customthe filtrate is purified by silica gel chromatography (toluene-ethyl acetate)

Sources & evidence

ORD record
ord-f0d16be3178f485790d00d67e75bf1ac
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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