HCID 60166734、化合物 → HCID 60166735、化合物

HRID 1485828ノート

反応式

HRID 1485828 の反応式
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

参加物

5

反応物 1

HCID 60166734HCID 60166734、化合物

生成物 1

HCID 60166735HCID 60166735、化合物収率 79%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e871066b8aa641be9f4fe7e9fc807739
出典データセット
uspto-grants-2016_08
特許番号
US09422320B2

反応ノート

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