Water → HCID 15750138, compound

HRID 256873Notes

Reaction equation

HRID 256873 reaction equation
C([Li])(C)(C)C.[CH3:6][O:7][C:8]1[CH:13]=[N:12][CH:11]=[C:10](I)[N:9]=1.[N:15]12[CH2:22][CH2:21][CH:18]([CH2:19][CH2:20]1)[CH2:17][C:16]2=O.[OH2:24]>CCCCC.CCOCC>[CH3:6][O:7][C:8]1[CH:13]=[N:12][CH:11]=[C:10]([C:17]2([OH:24])[CH:18]3[CH2:21][CH2:22][N:15]([CH2:20][CH2:19]3)[CH2:16]2)[N:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5661191-azabicyclo[2.2.2]octan-2-oneHCID 102634952-Iodo-6-methoxypyrazineHCID 178418306HCID 178418306, compound

Product 1

HCID 15750138HCID 15750138, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8003PentaneSolvent

Procedure

t-Butyllithium (20 ml of a 1.7M solution in pentane, 35.3 mmol) was added dropwise to a rapidly stirred solution of 2-methoxy-6-iodopyrazine (4.17 g, 17.6 mmol) in ether (80 ml), at -40° C. After 0.25 h a solution of quinuclidinone (2.21 g, 17.6 mmol) in ether (60 ml) was added dropwise and the reaction mixture warmed to room temperature and stirred for 2 h. Water (35 ml) was added and extracted with ethylacetate (4×100 ml). The combined extracts were dried (Na2SO4), the solvent removed under vacuum and, the residue chromatographed through alumina, eluting with dichloromethane/methanol (93:7) to give 3-[2-(6-methoxypyrazin)yl]-1-azabicyclo [2.2.2]octan-3-ol (1.65 g); δ (360 MHz, CDCl3) 1.37-1.51 (3H,m, --CH2 and CH of CH2); 1.70-1.90(1H, brs, OH); 1.94-1.96-(1H,m,CH); 2.20-2.32(1H,m,CH of CH2); 2.80-3.10(5H,m,2×CH2 and CH of CH2) 3.74(1H,dd, J=2 and 14.6 Hz, CH of CH2); 3.99(3H,s,Me); 8.15(1H,s,pyrazine-H); 8.39(1H,s,pyrazine-H).

Workup

  1. extractionextracted with ethylacetate (4×100 ml)
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. customthe solvent removed under vacuum
  4. customthe residue chromatographed through alumina
  5. washeluting with dichloromethane/methanol (93:7)

Sources & evidence

ORD record
ord-4e351bf433f1487b9ea597ebb07d7602
Source dataset
uspto-grants-1993_11
Patent number
US05260293

Reaction notes

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