Phenol → (S)-4-benzyl-2-(2-phenoxyethyl)piperazine-1-carboxylic acid tert-butyl ester

HRID 131401ノート

反応式

HRID 131401 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@@H:9]1[CH2:21][CH2:22][O:23]S(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I-].[Na+].[C:30]1(O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C)C=O.C(=O)(O)[O-].[Na+]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@@H:9]1[CH2:21][CH2:22][O:23][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 996PhenolHCID 5238Sodium IodideHCID 86604576(S)-4-benzyl-2-(2-methanesulfonyloxy-ethyl)piperazine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 69215534(S)-4-benzyl-2-(2-phenoxyethyl)piperazine-1-carboxylic acid tert-butyl ester収率 25%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

Combine (S)-4-benzyl-2-(2-methanesulfonyloxyethyl)piperazine-1-carboxylic acid tert-butyl ester (2.82 g, 7.08 mmol), sodium iodide (0.106 g, 0.708 mmol), and phenol (3.33 g, 35.4 mmol) in dimethyl formamide (40 mL) and stir at 100° C. for 20 hours. Dilute the mixture with saturated aqueous sodium bicarbonate and extract three times with dichloromethane. Combine the organic layers, dry over sodium sulfate and concentrate under reduced pressure. Purify by flash chromatography, eluting with a step gradient (100% dichloromethane to 5% 2N ammonia-methanol in dichloromethane) to obtain (S)-4-benzyl-2-(2-phenoxyethyl)piperazine-1-carboxylic acid tert-butyl ester (0.703 g, 25%): mass spectrum (APCI): m/z=397.2 (M+1).

後処理

  1. extractionextract three times with dichloromethane
  2. dry with materialdry over sodium sulfate
  3. concentrationconcentrate under reduced pressure
  4. customPurify by flash chromatography
  5. washeluting with a step gradient (100% dichloromethane to 5% 2N ammonia-methanol in dichloromethane)

出典と根拠

ORDレコード
ord-9910739c1c9941daa5f8519c0335ad00
出典データセット
uspto-grants-2008_06
特許番号
US07384934B2

反応ノート

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