Phthalimide → cis-N-[3-(2-pyridyl)cyclopentyl]phthalimide

HRID 655145Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@H:7]1[CH2:11][CH2:10][C@H:9](O)[CH2:8]1.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.C(C=P(CCCC)(CCCC)CCCC)#N>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@@H:7]1[CH2:11][CH2:10][C@H:9]([N:17]2[C:16](=[O:18])[C:15]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]3[C:13]2=[O:23])[CH2:8]1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of trans-3-(2-pyridyl)cyclopentanol (957 mg, 5.86 mmol) in THF (25 mL) was cooled to 0° C. and treated with phthalimide (1.29 g, 8.77 mmol), cyanomethylenetri-n-butylphosphorane (2.12 g, 8.78 mmol). The reaction mixture was stirred at 70° C. for 8 h. The solvent was removed, and the crude product was purified by column chromatography (Hexane/EtOAc=3/1→1/1) and triturated with Hexane-EtOAc to yield cis-N-[3-(2-pyridyl)cyclopentyl]phthalimide (901 mg, 53%) as a pale yellow powder.

Workup

customThe solvent was removed
customthe crude product was purified by column chromatography (Hexane/EtOAc=3/1→1/1)
customtriturated with Hexane-EtOAc

Sources & evidence

ORD record: ord-f9d73323bc6a47c7bb178cae29587b7d
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071591B2

Reaction notes

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