3-Hex-1-ynyl-5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridine → 5-Hexenyl-3-(1-methyl-2-(s)-pyrrolidinylmethoxy)pyridine

HRID 1780302Notes

Reaction equation

HRID 1780302 reaction equation
[C:1]([C:7]1[CH:8]=[C:9]([O:13][CH2:14][C@@H:15]2[CH2:19][CH2:18][CH2:17][N:16]2[CH3:20])[CH:10]=[N:11][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6]>CO.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[CH:1]([C:7]1[CH:8]=[C:9]([O:13][CH2:14][C@@H:15]2[CH2:19][CH2:18][CH2:17][N:16]2[CH3:20])[CH:10]=[N:11][CH:12]=1)=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 1

HCID 112195103-Hex-1-ynyl-5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridine

Product 1

HCID 698305875-Hexenyl-3-(1-methyl-2-(s)-pyrrolidinylmethoxy)pyridineYield 98%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-(1-hexynyl)-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine (from Example 4a, 100 mg, 0.37 mmol) in MeOH (3.0 mL) was added Lindlar's catalyst (10 mg). The mixture was stirred at room temperature overnight. The solvent was removed, and the residue was chromatographed on a silica gel column, eluting with NH4OH/MeOHTEtOAc 0:1:9 and 1:10:90 to afford a light yellowish oil (98 mg, 98%). MS (CI/NH3) m/z 277 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ0.88 (t, J=4.8 Hz, 3H), 1.23-1.37 (m, 6H), 1.53-1.62 (m, 2H), 1.70-2.08 (m, 4H), 2.26-2.36 (m, 1H), 2.48 (s, 3H), 2.56 (t, J=7.7 Hz, 2H), 2.58-2.71 (m, 1H), 3.07-3.14 (m, 1H), 3.88-4.05 (m, 2H), 7.03 (dd, J=3.0 Hz, J=J=2.1 Hz, 1H), 8.06 (d, J=2.1 Hz, 1H), 8.13 (d, J=3.0 Hz, 1H).

Workup

  1. customThe solvent was removed
  2. customthe residue was chromatographed on a silica gel column
  3. washeluting with NH4OH/MeOHTEtOAc 0:1:9 and 1:10:90

Sources & evidence

ORD record
ord-091c957fba944a3aa81aa26eebfdc6b1
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

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