Ethanol → tert-Butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate

HRID 1667306Notes

Reaction equation

HRID 1667306 reaction equation
O=[C:2]1[CH2:8][CH:7]2[N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:4]([CH2:5][CH2:6]2)[CH2:3]1.C1(C)C=CC(S([CH2:26][N+:27]#[C-])(=O)=O)=CC=1.CC(C)([O-])C.[K+].C(O)C>COCCOC>[C:26]([CH:2]1[CH2:8][CH:7]2[N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:4]([CH2:5][CH2:6]2)[CH2:3]1)#[N:27]

Participants

6

Reactant 4

HCID 702EthanolHCID 161915Tosylmethyl isocyanideHCID 2794767tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 53487658tert-Butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

tert-Butyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate was reacted in the presence of p-toluenesulfonylmethylisocyanide, potassium tert-butoxide and ethanol in 1,2-dimethoxyethane to produce tert-butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate.

Sources & evidence

ORD record
ord-8d3fee58ebb643c39eb5fe5a85e4f451
Source dataset
uspto-grants-2011_10
Patent number
US08044206B2

Reaction notes

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