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Triphenylphosphine → Benzyl 4-{(1R,2S)-2-[2-(4-bromo-2,5 difluorophenoxy)ethyl]cyclopropyl}piperidine-1-carboxylate

HRID 1474713
ノート
印刷プレビュー

反応式

HRID 1474713 の反応式
[OH:1][CH2:2][CH2:3][C@@H:4]1[CH2:6][C@@H:5]1[CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:9][CH2:8]1.[Br:23][C:24]1[C:29]([F:30])=[CH:28][C:27](O)=[C:26]([F:32])[CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C(Cl)Cl>[Br:23][C:24]1[C:29]([F:30])=[CH:28][C:27]([O:1][CH2:2][CH2:3][C@@H:4]2[CH2:6][C@@H:5]2[CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:14])[CH2:9][CH2:8]2)=[C:26]([F:32])[CH:25]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 70180424-Bromo-2,5-difluorophenolHCID 70856295Benzyl 4-((1R,2S)-2-(2-hydroxyethyl)cyclopropyl)piperidine-1-carboxylate

生成物 1

HCID 70818516Benzyl 4-{(1R,2S)-2-[2-(4-bromo-2,5 difluorophenoxy)ethyl]cyclopropyl}piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Benzyl 4-[(1R,2S)-2-(2-hydroxyethyl)cyclopropyl]piperidine-1-carboxylate (2.24 g, 7.38 mmol) in DCM (35 ml) was added 4-bromo-2,5-difluorophenol (1.62 g, 7.75 mmol), 3.93 g of triphenylphosphine (polymer-bound, 3.0 mmol/g) and di-tert-butyl diazene-1,2-dicarboxylate (2.21 g, 9.60 mmol). The reaction mixture was stirred at RT for 4 hours. The solid was removed by filtration through celite and the filtrate concentrated. The residue was purified by column chromatography on silica gel (Biotage column, 50 g SNAP) using a gradient 0-20% then 20% EtOAc in hexanes to afford the title compound. LC/MS (m/z): 496.2 (M+H)+.

後処理

  1. customThe solid was removed by filtration through celite
  2. concentrationthe filtrate concentrated
  3. customThe residue was purified by column chromatography on silica gel (Biotage column, 50 g SNAP)

出典と根拠

ORDレコード
ord-40ec5754d05941e5b1c56e69a4de1cac
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09018224B2

反応ノート

読み込み中…

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