Potassium Carbonate → 4-(4-Bromo-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1095070Notes

Reaction equation

HRID 1095070 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([O:10][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=2[CH:7]=[O:8])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 728635-BromosalicylaldehydeHCID 157347131-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine

Product 1

HCID 594280644-(4-Bromo-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl esterYield 95.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner similar to the method described in example 4a, 5-bromosalicylaldehyde (5.65 g, 28 mmol) (Aldrich) reacted with 4-(toluene-4-sulfonyloxy)-piperidine-1-carboxylic acid tert-butyl ester (5 g, 14 mmol, ASTATECH) and K2CO3 in N,N-dimethylformamide to give 4-(4-bromo-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester as a yellow gum (Yield 5.15 g, 51%).

Sources & evidence

ORD record
ord-e23fb0efdd3f4989b2994f23289e98c1
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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