5-(2-(4-Pyridinyl)vinyl)-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine → 5-(2-(4-Pyridinyl)ethyl)-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine

HRID 1780333ノート

反応式

HRID 1780333 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]2[CH:10]=[C:11]([O:15][CH2:16][C@@H:17]3[CH2:20][CH2:19][N:18]3[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:12]=[N:13][CH:14]=2)=[CH:3][CH:2]=1>CO.[Pd]>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]2[CH:10]=[C:11]([O:15][CH2:16][C@@H:17]3[CH2:20][CH2:19][N:18]3[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:12]=[N:13][CH:14]=2)=[CH:3][CH:2]=1

参加物

4

反応物 1

HCID 538525935-(2-(4-Pyridinyl)vinyl)-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine

生成物 1

HCID 228726405-(2-(4-Pyridinyl)ethyl)-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine収率 81.7%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

To a solution of 5-(2-(4-pyridinyl)vinyl)-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine from Example 59a (188 mg, 0.51 mmol) in methanol (10 mL) was added Pd/C (20 mg), and the mixture was stirred at room temperature for 40 hours. The catalyst was filtered off, and the solvent was removed under vacuum. The residue was chromatographed on a silica gel column, eluting with methylene chloride:methanol 10:2 to 10:5 to afford the title compound (154 mg). MS (CI/NH3) m/z 370 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.42 (s, 9H), 2.32 (m, 2H), 3.89 (m, 2H), 4.10 (m, 1H), 4.28 (m, 1H), 4.50 (m, 1H), 7.02 (m, 1H), 7.02 (m, 1H), 7.08 (m, 2H), 8.06 (m, 1H), 8.20 (m, 1H), 8.51 (m, 2H).

後処理

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed under vacuum
  3. customThe residue was chromatographed on a silica gel column
  4. washeluting with methylene chloride:methanol 10:2 to 10:5

出典と根拠

ORDレコード
ord-96cc771c29764703a3b4aca80a727126
出典データセット
uspto-grants-1997_05
特許番号
US05629325

反応ノート

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