Morpholine → [1-(3-Morpholin-4-yl-phenyl)ethyl]carbamic acid tert-butyl ester

HRID 2307418ノート

反応式

HRID 2307418 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[CH:12]=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=[CH:15][CH:16]=1)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>ClCCl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[CH:12]=1)[CH3:10])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 8083MorpholineHCID 62657Potassium Phosphate, TribasicHCID 86589152Trifluoro-methanesulfonic acid 3-(1-tert-butoxycarbonylaminoethyl)phenyl ester

生成物 1

HCID 69850623[1-(3-Morpholin-4-yl-phenyl)ethyl]carbamic acid tert-butyl ester収率 153.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

A mixture of trifluoro-methanesulfonic acid 3-(1-tert-butoxycarbonylaminoethyl)phenyl ester (1.5 g, 4.08 mmol), morpholine (8 mL) Pd2(dba)3 (187 mg, 5 mol %), di-t-butyl-biphenylphosphine (243 mg, 20 mol %), potassium phosphate (1.21 g, 5.71 mmol) was stirred at 80° C. in a sealed tube for 10 hours. After cooling down, the reaction mixture was diluted with dichloromethane (50 mL) and washed with water (10 mL). The aqueous layer was extracted with dichloromethane (2×15 mL) and the combined organic layer was dried over magnesium sulfate and concentrated under vacuum. The crude product was purified by flash chromatography of Biotage with 30% ethyl acetate/hexanes to provide the title compound as a pale yellow solid (1.01 g, 81% yield).

後処理

  1. temperatureAfter cooling down
  2. washwashed with water (10 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane (2×15 mL)
  4. dry with materialthe combined organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by flash chromatography of Biotage with 30% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-bc23ea6c09be49498922e6282e198ea3
出典データセット
uspto-grants-2004_12
特許番号
US06831080B2

反応ノート

読み込み中…