Water → HCID 57239737, compound

HRID 1034493Notes

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

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 with dilute aqueous sodium 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. NMR δ(CDCl3) ppm: 1.33, 1.42(2×s, 9H), 2.0 to 2.55(m, 2H), 3.02(s, 3H), 3.4 to 4.6(m, 5H), 5.15 to 5.3(m, 1H), 7.6 to 7.95(m, 4H). IR ν (CHCl3) cm-1 : 1775, 1716, 1693.

Workup

washsuccessively washed with dilute aqueous sodium hydroxide and water
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue is purified by 5% wet silica gel column chromatography

Sources & evidence

ORD record: ord-0657207b3ab7426f933c0a188ffbac42
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05317016

Reaction notes

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