Triethylamine → HCID 10204028, compound

HRID 2216382Notes

Reaction equation

HRID 2216382 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([N:15]2[CH2:19][CH:18]([O:20][CH3:21])[CH:17]([O:22][CH3:23])[CH2:16]2)[CH:11]=[CH:12][C:13]=1I)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([C@:26]1([OH:34])[CH:31]2[CH2:32][CH2:33][N:28]([CH2:29][CH2:30]2)[CH2:27]1)#[CH:25].C(N(CC)CC)C>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.CO.C(OCC)(=O)C>[CH2:1]([C:8]1[CH:9]=[C:10]([N:15]2[CH2:19][C@H:18]([O:20][CH3:21])[C@H:17]([O:22][CH3:23])[CH2:16]2)[CH:11]=[CH:12][C:13]=1[C:25]#[C:24][C@:26]1([OH:34])[CH:31]2[CH2:32][CH2:33][N:28]([CH2:29][CH2:30]2)[CH2:27]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 946095(3R)-3-ethynyl-1-azabicyclo[2.2.2]octan-3-olHCID 86591774HCID 86591774, compound

Product 1

HCID 10204028HCID 10204028, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Then, a mixture of 340 mg of (3R,4S)-1-(3-benzyl-4-iodophenyl-3,4-dimethoxypyrrolidine, 134 mg of (3R)-3-ethynyl-3-quinuclidinol (Production Example 22), 9 mg of tetrakis(triphenylphosphine)palladium (0), 8 mg of copper (I) iodide, 0.22 ml of triethylamine and 0.8 ml of methanol was stirred under nitrogen atmosphere at room temperature for 4 hours. After ethyl acetate and methanol were added to the reaction mixture for dissolution, NH-silica gel was added thereto and the reaction mixture was evaporated. The residue was subjected to column chromatography using NH-silica gel with 50% ethyl acetate/hexane and 0–2.5% methanol/ethyl acetate, to give 220 mg of the title compound.

Workup

  1. additionwas added
  2. customthe reaction mixture was evaporated

Sources & evidence

ORD record
ord-29887502b8414112bb752a5e6d02ec53
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Reaction notes

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