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Trifluoroacetic acid → 1-[1-(3-Methoxy-4-nitrophenyl)piperidin-4-yl]-4-methyl-1,4-azaphosphinane 4-oxide

HRID 921361
ノート
印刷プレビュー

反応式

HRID 921361 の反応式
[CH3:1][P:2]1(=[O:21])[CH2:7][CH2:6][N:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](OC(C)(C)C)=O)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+].FC1[CH:37]=[CH:38][C:39]([N+:44]([O-:46])=[O:45])=[C:40]([O:42][CH3:43])[CH:41]=1>C(Cl)Cl>[CH3:43][O:42][C:40]1[CH:41]=[C:14]([N:11]2[CH2:10][CH2:9][CH:8]([N:5]3[CH2:4][CH2:3][P:2](=[O:21])([CH3:1])[CH2:7][CH2:6]3)[CH2:13][CH2:12]2)[CH:37]=[CH:38][C:39]=1[N+:44]([O-:46])=[O:45]
参加物反応条件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 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 27792505-Fluoro-2-nitroanisoleHCID 67052687Tert-butyl 4-(4-methyl-4-oxido-1,4-azaphosphinan-1-yl)piperidine-1-carboxylate

生成物 1

HCID 681570431-[1-(3-Methoxy-4-nitrophenyl)piperidin-4-yl]-4-methyl-1,4-azaphosphinane 4-oxide収率 86%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

To a stirring solution of tert-butyl 4-(4-methyl-4-oxido-1,4-azaphosphinan-1-yl)piperidine-1-carboxylate (178 mg, 0.563 mmol) in CH2Cl2 (2 mL) was added trifluoroacetic acid (0.5 mL). After 20 min, the solution was concentrated and the resulting residue was redissolved in DMF (2 mL). Potassium carbonate (160 mg, 1.16 mmol) was added portionwise to the stirring solution followed by 5-fluoro-2-nitroanisole (158 mg, 0.930 mmol). The reaction mixture was heated to 50° C. After 2 h, the reaction mixture was concentrated and the residue was purified by silica gel chromatography (0-10% 7N ammonia in methanol:dichloromethane) to afford the compound as a bright yellow solid (176 mg, 86% yield).

後処理

  1. concentrationthe solution was concentrated
  2. dissolutionthe resulting residue was redissolved in DMF (2 mL)
  3. waitAfter 2 h
  4. concentrationthe reaction mixture was concentrated
  5. customthe residue was purified by silica gel chromatography (0-10% 7N ammonia in methanol:dichloromethane)

出典と根拠

ORDレコード
ord-a21b7c8d654543ea97729fb65aa36eff
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09273077B2

反応ノート

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