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

HRID 2305091Notes

Reaction equation

HRID 2305091 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/MeOH/EtOAc 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) δ 0.88 (t, J=4.8 Hz, 3H), 1.23-1.37 (m, 6 H), 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/MeOH/EtOAc 0:1:9 and 1:10:90

Sources & evidence

ORD record
ord-b960e4394b6c49e6b39b66e7770b28e4
Source dataset
uspto-grants-2002_08
Patent number
US06437138B1

Reaction notes

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