Hydrochloric Acid → methyl 4-[2-(4'-amino-1,1'-biphenyl-4-yl)-2-oxoethyl]tetrahydro-2H-pyran-4-carboxylate

HRID 9537노트

반응식

HRID 9537 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:28])[CH2:17][C:18]3([C:24]([O:26][CH3:27])=[O:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.Cl>C(O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16](=[O:28])[CH2:17][C:18]3([C:24]([O:26][CH3:27])=[O:25])[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[CH:14][CH:15]=2)=[CH:8][CH:9]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 21985756methyl 4-[2-(4'-nitro-1,1'-biphenyl-4-yl)-2-oxoethyl]tetrahydro-2H-pyran-4-carboxylate

생성물 1

HCID 21985793methyl 4-[2-(4'-amino-1,1'-biphenyl-4-yl)-2-oxoethyl]tetrahydro-2H-pyran-4-carboxylate수율 91.4%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

실험 절차

To a solution of methyl 4-[2-(4′-nitro-1,1′-biphenyl-4-yl)-2-oxoethyl]tetrahydro-2H-pyran-4-carboxylate (1.24 g, 3.25 mmol) in 85% ethanol (50 mL) was added iron powder (1.81 g), followed by 2 N aqueous HCl (1.62 mL), and the resulting mixture was refluxed for 2.5 h. The mixture was then filtered through a pad of Celite® and the filtrate was extracted with dichloromethane. The combined organic phases were then dried over anhydrous sodium sulfate and concentrated in vacuo to afford methyl 4-[2-(4′-amino-1,1′-biphenyl-4-yl)-2-oxoethyl]tetrahydro-2H-pyran-4-carboxylate (1.05 g, 91%). LC-MS ret. time 2.20; m/z 354.0 (MH+); 1H NMR (300 MHz, CDCl3) δ 1.57–1.66 (m, 2H), 2.09 (m, 2H), 3.28 (s, 2H), 3.61 (s, 3H), 3.64–3.71 (m, 4H), 6.76 (d, 2H), 7.42 (d, 2H), 7.54 (d, 2H), 7.88 (d, 2H).

후처리

  1. temperaturethe resulting mixture was refluxed for 2.5 h
  2. filtrationThe mixture was then filtered through a pad of Celite®
  3. extractionthe filtrate was extracted with dichloromethane
  4. dry with materialThe combined organic phases were then dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ffffb01d3bdd4e01bba1881b67a7067c
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091228B2

반응 노트

불러오는 중…