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 1780333Notes

Reaction equation

HRID 1780333 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-96cc771c29764703a3b4aca80a727126
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

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