4-[4-(1,4,7-Trioxaoct-1-yl)phenyl]-N-benzyloxycarbonylbutylamine → 4-[4-(1,4,7-Trioxaoct-1-yl)phenyl]butylamine

HRID 81315노트

반응식

HRID 81315 반응식
[O:1]([C:9]1[CH:14]=[CH:13][C:12]([CH:15](C(OCC2C=CC=CC=2)=O)[CH2:16][CH2:17][CH2:18][NH2:19])=[CH:11][CH:10]=1)[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH3:8]>C(O)C.[Pd]>[O:1]([C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])=[CH:13][CH:14]=1)[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH3:8]

참가 물질

4

반응물 1

HCID 673669224-[4-(1,4,7-Trioxaoct-1-yl)phenyl]-N-benzyloxycarbonylbutylamine

생성물 1

HCID 225661364-[4-(1,4,7-Trioxaoct-1-yl)phenyl]butylamine수율 99.1%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

Compound 106 (800 mg, 2.0 mmol) in ethanol (20 mL), was subjected to 1 atmosphere of H2 in the presence of 10% palladium on carbon (100 mg, cat.) with stirring for 5 h. After standing overnight, the reaction was purged with N2 then suction filtered through celite and washed off the celite with methylene chloride. The solvents were evaporated and chromatographed (silica gel, 200:10:1 methylene chloride/methanol/concentrated ammonium hydroxide) to afford 530 mg (>99%) of amine 107. 1H NMR (300 MHz, CDCl3) δ 1.31 (br s, 2H), 1.41-1.52 (m, 2H), 1.55-1.67 (m, 2H), 2.56 (t, J=7.7 Hz, 2H), 2.70 (t, J=7.0 Hz, 2H), 3.39 (s, 3H), 3.58 (m, 2H), 3.72 (m, 2H), 3.84 (t, J=4.9 Hz, 2H), 4.12 (t, J=5.3 Hz, 2H), 6.83 (d, J=8.7 Hz, 2H), 7.07 (d, J=8.7 Hz, 2H). CI MS m/z=268 [C15H25NO3+H]+.

후처리

  1. waitAfter standing overnight
  2. customthe reaction was purged with N2
  3. filtrationthen suction filtered through celite
  4. washwashed off the celite with methylene chloride
  5. customThe solvents were evaporated
  6. customchromatographed (silica gel, 200:10:1 methylene chloride/methanol/concentrated ammonium hydroxide)

출처 및 근거

ORD 기록
ord-c136a85be6c647c2b4875f245120e84c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846688B2

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