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 2305118Notes

Reaction equation

HRID 2305118 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)ethenyl)-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine from Example 59a (188 mg, 0.51 mmol) in MeOH (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 CH2Cl2:MeOH 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) δ 1.42 (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 CH2Cl2:MeOH 10:2 to 10:5

Sources & evidence

ORD record
ord-6d97fac481ba4a6892564ed7eb9ba8e0
Source dataset
uspto-grants-2002_08
Patent number
US06437138B1

Reaction notes

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