Acetyl chloride → HCID 20303318, compound

HRID 1448639Notes

Reaction equation

HRID 1448639 reaction equation
[CH2:1]([N:8]1[CH:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]2[CH2:21][CH:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:9]1[CH:10]=[CH:11]2)[C:2]1C=CC=CC=1.[H][H].C(C1C2CC(C(OCC)=[O:46])C(C=C2)N1)C1C=CC=CC=1.C(Cl)(=O)C>[Pd].N1C=CC=CC=1>[C:1]([N:8]1[CH:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]2[CH2:21][CH:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:9]1[CH:10]=[CH:11]2)(=[O:46])[CH3:2]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 12880795HCID 12880795, compoundHCID 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-carboxylate 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-9eb61058309542df9e05b93042c70d15
Source dataset
uspto-grants-1979_12
Patent number
US04180667

Reaction notes

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