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

HRID 920584노트

반응식

HRID 920584 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
120 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-90581374fad244ec972668292d2ee387
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273017B2

반응 노트

불러오는 중…