Potassium Carbonate → (r/s)-3-(4-Bromo-2-formyl-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1095090Notes

Reaction equation

HRID 1095090 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[CH2:22][CH2:21][C@H:20](OS(C)(=O)=O)[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[CH2:22][CH2:21][CH:20]([O:10][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=2[CH:7]=[O:8])[CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 728635-BromosalicylaldehydeHCID 11032777(S)-1-Boc-3-methanesulfonyloxy-pyrrolidine

Product 1

HCID 57743437(r/s)-3-(4-Bromo-2-formyl-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner similar to the method described in example 4a, 5-bromosalicylaldehyde (3.6 g, 18 mmol) (Aldrich) reacted with (S)-3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester (5.3 g, 20 mmol) and K2CO3 in N,N-dimethylformamide to give (R/S)-3-(4-bromo-2-formyl-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester as an orange oil (Yield 3.6 g, 54%).

Sources & evidence

ORD record
ord-3026fba527cf4c96922155f334481352
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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