Phthalimide potassium salt → HCID 57222945, compound

HRID 1034498Notes

Reaction equation

HRID 1034498 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][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[O:23])(=O)=O)=CC=1.[C:35]1(=[O:45])[NH:39][C:38](=[O:40])[C:37]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:36]12.[K]>CN(C)C=O>[CH3:33][O:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][O:24][C:22]([N:13]2[CH2:14][C@H:15]([O:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:16][C@H:12]2[CH2:11][N:39]2[C:38](=[O:40])[C:37]3=[CH:41][CH:42]=[CH:43][CH:44]=[C:36]3[C:35]2=[O:45])=[O:23])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 131718418HCID 131718418, compound

Product 1

HCID 57222945HCID 57222945, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol p-toluenesulfonate (6.35 g: 12.27 mmole) in dimethylformamide (60 ml), potassium phthalimide (2.7 g) is added. The mixture is stirred at 70° C. for 4 hours. The reaction mixture is poured into ice water and extracted with ethyl acetate. The extract is 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=2:1) to give (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-methanesulfonyloxy-2-phthalimidomethylpyrrolidine (4.65 g). Yield: 77.5%. NMR δ(CDCl3) ppm: 2 to 2.3(m, 1H), 2.4 to 2.6(m, 1H), 2.95, 2.97(2×s, 3H), 3.43 to 4.2(m, 5H), 3.80(s, 3H), [5.01(s)+5.07, 4.96(ABq, 12.2 Hz), 2H], 5.13 to 5.3(m, 1H). IR ν (CHCl3) cm-1 : 1774, 1716, 1613.

Workup

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

Sources & evidence

ORD record
ord-86208bddf2594c938af29baa8bf80196
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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