Phthalimide → 2-(2-Phenyl-3-pyrrolidin-1-yl propyl)isoindole-1,3-dione

HRID 645482Notes

Reaction equation

[C:1]1([CH:7]([CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:8]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.OS([O-])(=O)=O.[K+]>C1COCC1.O>[C:1]1([CH:7]([CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:8][N:20]2[C:16](=[O:26])[C:17]3[C:18](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:19]2=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-phenyl-3-pyrrolidin-1-yl propan-1-ol (3.4 mmol) in THF (10 mL) is successively added phthalimide (4.1 mmol), triphenylphosphine (5.1 mmol) and diethyl azodicarboxylate (5.1 mmol) at 0° C., then the mixture is stirred at 0° C. for 1.5 h. After dilution with water, the mixture is acidified to pH<3 with aq. KHSO4 then washed with AcOEt. The aqueous layer basified to pH>11 with sat aq. NaHCO3 then extracted with AcOEt. The organic extracts are washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue is triturated with ether to give 2-(2-phenyl-3-pyrrolidin-1-yl propyl)isoindole-1,3-dione, which is directly used for the next reaction without further purification.

Workup

customat 0° C.
washthen washed with AcOEt
extractionthen extracted with AcOEt
washThe organic extracts are washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue is triturated with ether

Sources & evidence

ORD record: ord-ba33bcabb5964ad19f8646181d4fd913
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07704996B2

Reaction notes

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