Ammonia → HCID 10135633, compound

HRID 2216380Notes

Reaction equation

HRID 2216380 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])=[CH:9][C:8]=1[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=O)=O.[C:28]([C@:30]1([OH:38])[CH:35]2[CH2:36][CH2:37][N:32]([CH2:33][CH2:34]2)[CH2:31]1)#[CH:29].C(N(CC)CC)C.N>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.CN(C)C=O>[CH2:19]([C:8]1[CH:9]=[C:10]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH:11]=[CH:12][C:7]=1[C:29]#[C:28][C@:30]1([OH:38])[CH:35]2[CH2:36][CH2:37][N:32]([CH2:33][CH2:34]2)[CH2:31]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 946095(3R)-3-ethynyl-1-azabicyclo[2.2.2]octan-3-olHCID 21942297HCID 21942297, compound

Product 1

HCID 10135633HCID 10135633, compoundYield 32.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 200 mg of 2-benzyl-4-[2-pyrrolidinon-1-yl]phenyl trifluoromethanesulfonate (Production Example 5), 80 mg of (3R)-3-ethynyl-3-quinuclidinol (Production Example 22), 30 mg of tetrakis(triphenylphosphine)palladium (0), 5 mg of copper (I) iodide and 0.2 ml of triethylamine was added 1 ml of N,N-dimethylformamide, followed by heating under stirring under nitrogen atmosphere in an oil bath at 80° C. for 3 hours. After standing to cool, aqueous ammonia was added to the reaction mixture, which then was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed and the residue was purified by NH-silica gel column chromatography with ethyl acetate, to give 66 mg of the title compound.

Workup

  1. temperatureby heating
  2. temperatureto cool
  3. extractionthen was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed
  7. customthe residue was purified by NH-silica gel column chromatography with ethyl acetate

Sources & evidence

ORD record
ord-cefab924e094407995dc8dcc00e9b764
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Reaction notes

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