Phthalimide potassium salt → HCID 57001573, compound

HRID 1941597Notes

Reaction equation

HRID 1941597 reaction equation
C1(C)C=CC(S(O[CH2:11][C@@H:12]2[CH2:16][C@@H:15]([OH:17])[CH2:14][N:13]2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[O:19])(=O)=O)=CC=1.[C:31]1(=[O:41])[NH:35][C:34](=[O:36])[C:33]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:32]12.[K]>CN(C)C=O.C(OCC)(=O)C>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][O:20][C:18]([N:13]2[CH2:14][C@H:15]([OH:17])[CH2:16][C@H:12]2[CH2:11][N:35]2[C:34](=[O:36])[C:33]3=[CH:37][CH:38]=[CH:39][CH:40]=[C:32]3[C:31]2=[O:41])=[O:19])=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 131718419HCID 131718419, compound

Product 1

HCID 57001573HCID 57001573, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-hydroxypyrrolidine-2-methanol p-toluenesulfonate (24 g: 55.1 mmole) in dimethylformamide (200 ml), potassium phthalimide (15.3 g) is added. The mixture is stirred at 80° C. for 4 hours. The reaction mixture is diluted with ethyl acetate, successively washed with water and brine, dried over magnesium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography (toluene: ethyl acetate=1:2) to give (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-hydroxy-2-phthalimidomethylpyrrolidine (18.1 g). Yield: 80%.

Workup

  1. washsuccessively washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by silica gel column chromatography (toluene: ethyl acetate=1:2)

Sources & evidence

ORD record
ord-f95b4a003ef44118b874eb76c5701941
Source dataset
uspto-grants-1997_12
Patent number
US05703243

Reaction notes

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