Methanol → 1-Azabicyclo[2.2.2]octan-3-ol, 3-(3-methoxypyrazinyl)-

HRID 1646930Notes

Reaction equation

HRID 1646930 reaction equation
Cl[C:2]1[C:3]([C:8]2([OH:16])[CH:13]3[CH2:14][CH2:15][N:10]([CH2:11][CH2:12]3)[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.[CH3:17][OH:18]>>[CH3:17][O:18][C:2]1[C:3]([C:8]2([OH:16])[CH:13]3[CH2:14][CH2:15][N:10]([CH2:11][CH2:12]3)[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 103318403-(3-Chloropyrazinyl)-1-azabicyclo[2.2.2]octan-3-ol

Product 1

HCID 103540531-Azabicyclo[2.2.2]octan-3-ol, 3-(3-methoxypyrazinyl)-

Procedure

To a solution of 40 ml of methanol that had reacted with 0.5 g of Na (0.022 mol) was added 0.5 g of (7) (0.0021 mol). The reaction was heated to reflux for 1 h followed by evaporation of the solvent. The residue was treated with ice-water and extracted 3× with 25 ml of CH2Cl2. The extracts were dried and evaporated to give a yellow solid that was recrystallized from ethyl acetate to give (8), 0.12 g, mp 130°-131° C. NMR ppm (CDCl3) 1.15 (1H, m), 1.45 (2H, m), 2.25 (1H, m), 2.38 (1H, m), 2.7-3.15 (5H, m), 3.9 (1H, bs), 4.05 (3H, s), 4.3 (1H, d), 8.05 (1H, d), 8.15 (1H, d). Anal. C12H17N3O2 requires C: 61.26; H: 7.28; N: 17.86%. Found C: 61.02; H: 7.45; N: 17.95%.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 1 h
  3. customfollowed by evaporation of the solvent
  4. additionThe residue was treated with ice-water
  5. extractionextracted 3× with 25 ml of CH2Cl2
  6. customThe extracts were dried
  7. customevaporated
  8. customto give a yellow solid
  9. customthat was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b0aee7f0c0df49878816efd4235e738e
Source dataset
uspto-grants-1993_01
Patent number
US05182283

Reaction notes

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