Sodium Iodide → 3-[2-(4-Octyloxy-phenyl)-morpholin-4-yl]-butyric acid tert-butyl ester

HRID 920584ノート

反応式

HRID 920584 の反応式
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[O:21][CH2:20][CH2:19][NH:18][CH2:17]2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:22]([O:26][C:27](=[O:32])[CH2:28][CH:29](Br)[CH3:30])([CH3:25])([CH3:24])[CH3:23].[I-].[Na+].C1CCN2C(=NCCC2)CC1>CC#N>[C:22]([O:26][C:27](=[O:32])[CH2:28][CH:29]([N:18]1[CH2:19][CH2:20][O:21][CH:16]([C:13]2[CH:12]=[CH:11][C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:15][CH:14]=2)[CH2:17]1)[CH3:30])([CH3:25])([CH3:24])[CH3:23]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57092335Tert-butyl 3-bromobutanoateHCID 670323512-(4-Octyloxy-phenyl)-morpholine

生成物 1

HCID 670324853-[2-(4-Octyloxy-phenyl)-morpholin-4-yl]-butyric acid tert-butyl ester収率 31.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
120 °C

実験手順

A mixture of 2-(4-octyloxy-phenyl)-morpholine (0.24 gram, 1.1 mmol), 3-bromobutyric acid tert-butyl ester (0.24 g; 1.1 mmol), sodium iodide (27.4 mg; 0.2 mmol), and DBU (0.4 mL; 2.7 mmol) in CH3CN (10 mL) was heated in a closed vessel at 120° C. After cooling to RT the reaction mixture was partitioned between 5% aqueous NaHCO3 solution and EtOAc. The layers were separated and the organic layer was dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography (SiO2, Et2O) to afford 3-[2-(4-octyloxy-phenyl)-morpholin-4-yl]-butyric acid tert-butyl ester (0.15 g).

後処理

  1. temperatureAfter cooling to RT the reaction mixture
  2. customwas partitioned between 5% aqueous NaHCO3 solution and EtOAc
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (SiO2, Et2O)

出典と根拠

ORDレコード
ord-90581374fad244ec972668292d2ee387
出典データセット
uspto-grants-2016_03
特許番号
US09273017B2

反応ノート

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