Acetyl chloride → HCID 20303318, compound

HRID 866568Notes

Reaction equation

HRID 866568 reaction equation
[H][H].[CH2:3]([CH:10]1[CH:15]2[CH2:16][CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:12]([CH:13]=[CH:14]2)[NH:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:23](Cl)(=[O:25])[CH3:24]>[Pd].N1C=CC=CC=1>[C:23]([N:11]1[CH:10]([CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:15]2[CH2:16][CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:12]1[CH:13]=[CH:14]2)(=[O:25])[CH3:24]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 20303309HCID 20303309, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20303318HCID 20303318, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049PyridineSolvent

Procedure

Reduction of the ethyl 2,3-dibenzyl-2-azabicyclo[2.2.2]oct-5-ene-7-carboxylic described in Example 1AE in the form of the hydrochloride salt with one molar equivalent of hydrogen over a palladium-on-charcoal catalyst at ambient temperature and reaction of the resulting ethyl 3-benzyl-2-azabicyclo[2.2.2]oct-5-ene-7-carboxylate with acetyl chloride in the presence of pyridine affords ethyl 2-acetyl-3-benzyl-2-azabicyclo[2.2.2]oct-5-ene-7-carboxylate.

Sources & evidence

ORD record
ord-d856489250eb433197188c4fbda7f549
Source dataset
uspto-grants-1978_07
Patent number
US04100164

Reaction notes

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