Phthalimide → trans-N-[3-(1H-pyrazol-1-yl)cyclopentyl]phthalimide

HRID 655150Notes

Reaction equation

[N:1]1([C@@H:6]2[CH2:10][CH2:9][C@H:8](O)[CH2:7]2)[CH:5]=[CH:4][CH:3]=[N:2]1.[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[N:1]1([C@H:6]2[CH2:10][CH2:9][C@H:8]([N:16]3[C:15](=[O:17])[C:14]4=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]4[C:12]3=[O:22])[CH2:7]2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of cis-3-(1H-pyrazol-1-yl)cyclopentanol (5.01 g, 32.9 mmol) in THF (150 mL) was cooled to 0° C. and treated with phthalimide (5.33 g, 36.2 mmol), diisopropylazodicarboxylate (7.1 mL, 36.1 mmol) and triphenylphosphine (9.48 g, 36.1 mmol). The reaction mixture was stirred at 0° C. for 4 h. The reaction mixture was poured water and then extracted with EtOAc. The organic layer was dried over anhyd Na2SO4 followed by the removal of solvent. The crude product was purified by column chromatography (Chromatrex, Hexane/EtOAc=5/1) to yield trans-N-[3-(1H-pyrazol-1-yl)cyclopentyl]phthalimide (4.85 g, 52%) as a colorless powder.

Workup

extractionextracted with EtOAc
dry with materialThe organic layer was dried over anhyd Na2SO4
customfollowed by the removal of solvent
customThe crude product was purified by column chromatography (Chromatrex, Hexane/EtOAc=5/1)

Sources & evidence

ORD record: ord-ba091a7c1c0f4b9cbcd287eff98e2698
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071591B2

Reaction notes

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