HCID 12880752, compound → HCID 20303298, compound

HRID 1732979Notes

Reaction equation

HRID 1732979 reaction equation
Cl.C([N:9]1[CH:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]2[CH2:22][CH:23]([C:24](OCC)=[O:25])[CH:10]1[CH:11]=[C:12]2[CH3:29])C1C=CC=CC=1.C(C1C2CC(C(OCC)=O)C(C=C2C)N1)C1C=CC=CC=1>>[CH2:15]([CH:14]1[NH:9][C:24](=[O:25])[CH:23]2[CH2:22][CH:13]1[C:12](=[CH2:29])[CH:11]=[CH:10]2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 12880752HCID 12880752, compoundHCID 20303335HCID 20303335, compound

Product 1

HCID 20303298HCID 20303298, compound

Procedure

Following a procedure similar to that described in Example 15A, catalytic debenzylation of the ethyl 2,3-dibenzyl-5-methyl-2-azabicyclo[2.2.2]oct-5-ene-7-carboxylate hydrochloride described in Example 1F and base catalyzed rearrangement of the resulting ethyl 3-benzyl-5-methyl-2-azabicyclo[2.2.2]oct-5-ene-7-carboxylate affords 2-benzyl-8-methylene-3-azabicyclo[3.3.1]non-6-en-4-one.

Sources & evidence

ORD record
ord-f0968b1f051d44be95e51c9b5b3d18fc
Source dataset
uspto-grants-1980_12
Patent number
US04239890

Reaction notes

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