Ethyl chloroformate → 1-Ethyl 4-methyl 4-(4-but-2-ynyloxybenzenesulfonyl)-1,4-piperidinedicarboxylate

HRID 353571Notes

Reaction equation

HRID 353571 reaction equation
[CH3:1][O:2][C:3]([C:5]1([S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]#[C:23][CH3:24])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4].C(=O)(O)[O-].[Na+].[CH2:30]([O:32][C:33](Cl)=[O:34])[CH3:31]>C(Cl)(Cl)Cl>[CH2:21]([O:20][C:17]1[CH:16]=[CH:15][C:14]([S:11]([C:5]2([C:3]([O:2][CH3:1])=[O:4])[CH2:10][CH2:9][N:8]([C:33]([O:32][CH2:30][CH3:31])=[O:34])[CH2:7][CH2:6]2)(=[O:13])=[O:12])=[CH:19][CH:18]=1)[C:22]#[C:23][CH3:24]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 54136994HCID 54136994, compound

Product 1

HCID 599039491-Ethyl 4-methyl 4-(4-but-2-ynyloxybenzenesulfonyl)-1,4-piperidinedicarboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-(4-but-2-ynyloxy-benzenesulfonyl)-piperidine-4-carboxylic acid methyl ester (400 mg, 1.03 mmol) in chloroform (10 ml) was added sodium bicarbonate (865 mg, 10.3 mmol), ethylchloroformate (0.147 ml, 1.54 mmol). The resulting mixture was stirred for 15 hours at room temperature, quenched with water and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and concentrated to give 425 mg (98%) of the product as a solid. MS-ES: m/z 424.4 (M+H)+.

Workup

  1. customquenched with water
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a5a062975e4c486199eb4dba0414767a
Source dataset
uspto-grants-2004_06
Patent number
US06753337B2

Reaction notes

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