HCID 60166734, 화합물 → HCID 60166735, 화합물

HRID 1485828노트

반응식

HRID 1485828 반응식
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:21][CH2:22][NH:23][C:24](=[O:26])[CH3:25])=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:14]=1)C1C=CC=CC=1>[Pd].CO.C(Cl)Cl>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:21][CH2:22][NH:23][C:24](=[O:26])[CH3:25])=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:14]=1

참가 물질

5

반응물 1

HCID 60166734HCID 60166734, 화합물

생성물 1

HCID 60166735HCID 60166735, 화합물수율 79%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

Palladium on carbon (10%, 5 mg) was added to 8a (120 mg, 0.35 mmol) in degassed MeOH (3.5 mL) and the solution was placed under an atmosphere of H2. After 12 h, the solution was diluted with DCM and filtered through Celite. The eluent was concentrated to afford a yellow solid, which was purified by column chromatography (SiO2, 100:5, DCM:MeOH) to afford phenol 9a (64 mg, 0.25 mmol, 79%) as a pale yellow amorphous solid. 1H NMR (400 MHz, CDCl3) δ 7.25-7.14 (m, 5H), 7.11-7.05 (m, 1H), 6.90 (d, J=8.3 Hz, 1H), 6.64 (d, J=8.3 Hz, 1H), 6.59 (d, J=2.5 Hz, 1H), 5.61 (t, J=5.5 Hz, 1H), 3.12-3.02 (m, 2H), 2.55 (t, J=7.1 Hz, 2H), 1.66 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 171.2, 155.2, 143.4, 141.6, 130.8, 129.1, 128.4, 127.2, 127.2, 117.4, 115.0, 41.1, 31.8, 23.2; HRMS m/z: [M+Na+] for C16H17NO2Na, calcd, 278.1151. found, 278.1155.

후처리

  1. filtrationfiltered through Celite
  2. concentrationThe eluent was concentrated
  3. customto afford a yellow solid, which
  4. customwas purified by column chromatography (SiO2, 100:5, DCM:MeOH)

출처 및 근거

ORD 기록
ord-e871066b8aa641be9f4fe7e9fc807739
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422320B2

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