Acetonedicarboxylic acid → 8-Benzyl-8-azabicyclo(3.2.1)octan-3-one

HRID 28517

Reaction equation

HRID 28517 reaction equation
N[C@@:2]12[N:9]([CH3:10])[C@@H:6]([CH2:7][CH2:8]1)[CH2:5][CH2:4][CH2:3]2.[CH3:11]OC1CCC(OC)O1.[CH2:20]([C:27](O)=O)[C:21]([CH2:23][C:24](O)=[O:25])=O>>[CH2:2]([N:9]1[CH:10]2[CH2:27][CH2:20][CH:21]1[CH2:23][C:24](=[O:25])[CH2:11]2)[C:8]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 68328Acetonedicarboxylic acidHCID 790982,5-DimethoxytetrahydrofuranHCID 67082042Amino tropane

Product 1

HCID 1198468-Benzyl-8-azabicyclo(3.2.1)octan-3-one

Procedure

For example, the protected aminotropane intermediate 16 can be prepared by reacting 2,5-dimethoxy tetrahydrofuran 17 with 1,3-acetonedicarboxylic acid 18 to provide 8-benzyl-8-azabicyclo[3.2.1]octan-3-one 19, commonly N-benzyltropanone. N-benzyltropanone is then reacted with a slight excess of di-tert-butyl dicarbonate in the presence of a transition metal catalyst to provide the protected Boc intermediate 20, which is reduced to provide the protected aminotropane intermediate 16.

Sources & evidence

ORD record
ord-dd6f8a06142f4aa1b15ab253a9404259
Source dataset
uspto-grants-2008_09
Patent number
US07419989B2

Linked notes

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