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

HRID 1095093Notes

Reaction equation

HRID 1095093 reaction equation
[I: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]([I: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 2526125-IodosalicylaldehydeHCID 11032777(S)-1-Boc-3-methanesulfonyloxy-pyrrolidine

Product 1

HCID 57743241(r/s)-3-(2-Formyl-4-iodo-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner similar to the method described in example 4a, 5-iodosalicylaldehyde (5 g, 20 mmol) (Aldrich) reacted with (S)-3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester (7 g, 26 mmol) prepared in Example 48a and K2CO3 in N,N-dimethylformamide to give (R/S)-3-(2-formyl-4-iodo-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester as a white foam (Yield 5 g, 60%).

Sources & evidence

ORD record
ord-c215b3e34d5c46938f50c13f6caf2ce6
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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