Tyramine → HCID 59717865, compound

HRID 2197616Notes

Reaction equation

HRID 2197616 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[C:11](=[O:18])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])N.F[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:14]([O:13][C:11](=[O:18])[NH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[CH:6][CH:5]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 5610TyramineHCID 9590p-FluoronitrobenzeneHCID 10796Cesium carbonateHCID 77922tert-Butyl carbamate

Product 1

HCID 59717865HCID 59717865, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

As shown in scheme 5, tyramine is protected as the t-butyl carbamate 22 and then reacted with 4-fluoronitrobenzene with cesium carbonate in DMF to yield the corresponding biarylether, {2-[4-(4-nitro-phenoxy)-phenyl]ethyl}-carbamic acid tert-butyl ester (19). Compound 19 is reduced by catalytic hydrogenation with palladium on carbon at the nitro group to afford the amine 23. Compound 23 is then N-acylated with acetyl chloride to afford the N-acyl compound 25. The t-Boc protecting group is removed from compound 25 using TFA in dichloromethane and the resulting amine 26 is reacted with various aldehydes under reductive amination conditions to afford compound 27.

Sources & evidence

ORD record
ord-cc6a7bc7dcd3432d8513036978a86dd4
Source dataset
uspto-grants-2012_12
Patent number
US08338611B2

Reaction notes

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