Phthalimide potassium salt → HCID 57001573, compound

HRID 1034503Notes

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

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%. NMR δ(CDCl3) ppm: 1.9 to 2.2(m, 2H), 3.4 to 4.05(m, 5H), 3.80(s, 3H), 4.3 to 4.6(m, 2H), 4.8 to 5.1(m, 2H), 6.83(d, J=8.2 Hz, 2H), 7.25(d, J=8.2 Hz, 2H), 7.6 to 7.9(m, 4H). IR ν (CHCl3) cm-1 : 3458, 1773, 1712.

Workup

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

Sources & evidence

ORD record: ord-59fe38f3dda04e42bf71bc6a06e25034
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05317016

Reaction notes

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