Water → HCID 57239737, compound

HRID 1941586Notes

Reaction equation

HRID 1941586 reaction equation
C1(C)C=CC(S(O[CH2:11][C@@H:12]2[CH2:16][C@@H:15]([O:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][N:13]2[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])(=O)=O)=CC=1.[C:30]1(=[O:40])[NH:34][C:33](=[O:35])[C:32]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:31]12.[K].O.C(OCC)(=O)C>CN(C)C=O>[C:25]([O:24][C:22]([N:13]1[CH2:14][C@H:15]([O:17][S:18]([CH3:21])(=[O:19])=[O:20])[CH2:16][C@H:12]1[CH2:11][N:34]1[C:33](=[O:35])[C:32]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:31]2[C:30]1=[O:40])=[O:23])([CH3:26])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24194345Phthalimide potassium saltHCID 131718417HCID 131718417, compound

Product 1

HCID 57239737HCID 57239737, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (2S,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol p-toluenesulfonate (20.78 g) in dimethylformamide(200 ml), potassium phthalimide (9.61 g) is added. The mixture is stirred at 70° C. for 3 hours. The reaction mixture is poured into a mixture of water and ethyl acetate. The organic layer is taken, successively washed withsodium sulfate, and co hydroxide and water, dried over sodium sulfate, and concentrated in vacuo. The residue is purified by 5% wet silica gel column chromatography to give (2S,4R)-1-t-butoxycarbonyl-2-phthalimidomethyl-4-methanesulfonyloxypyrrolidine (11.17 g). Yield: 60%. Colorless foam.

Workup

  1. washsuccessively washed withsodium sulfate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by 5% wet silica gel column chromatography

Sources & evidence

ORD record
ord-9327728b0f5b4496a77f4094dc65c313
Source dataset
uspto-grants-1997_12
Patent number
US05703243

Reaction notes

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