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

HRID 655150ノート

反応式

HRID 655150 の反応式
[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

参加物

7

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 67133889cis-3-(1H-pyrazol-1-yl)cyclopentanol

生成物 1

HCID 67133690trans-N-[3-(1H-pyrazol-1-yl)cyclopentyl]phthalimide収率 52.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-ba091a7c1c0f4b9cbcd287eff98e2698
出典データセット
uspto-grants-2011_12
特許番号
US08071591B2

反応ノート

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