Methyl chloroformate → HCID 66915644, compound

HRID 656496Notes

Reaction equation

HRID 656496 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]3([CH2:17][CH2:16][CH2:15][N:14]4[CH:18]=[N:19][CH:20]=[C:13]34)[C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1.[H-].[Na+].Cl[C:24]([O:26][CH3:27])=[O:25]>CN(C)C=O.O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]3([CH2:17][CH2:16][CH2:15][N:14]4[CH:18]=[N:19][CH:20]=[C:13]34)[C:8](=[O:12])[N:9]2[C:24]([O:26][CH3:27])=[O:25])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 66915571HCID 66915571, compound

Product 1

HCID 66915644HCID 66915644, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1 mmol of 6′-methoxy-6,7-dihydro-5H-spiro[imidazo[1,5-a]pyridine-8,3′-indol]-2′(1′H)-one in 5 ml of N,N-dimethyl formamide is treated with 1.2 mmol of sodium hydride (60% dispersion in oil). The reaction mixture is stirred for 20 minutes at room temperature, then 1.2 mmol of methyl chloroformate are added. The reaction mixture is stirred for 20 minutes at room temperature, then diluted with water and extracted with tert-butyl methyl ether (3×). The combined organic phases are dried with sodium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60F) on the basis of the Rf value.

Workup

  1. stirringThe reaction mixture is stirred for 20 minutes at room temperature
  2. extractionextracted with tert-butyl methyl ether (3×)
  3. dry with materialThe combined organic phases are dried with sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-d8ca5772447447ffa9a26bc81f8cb439
Source dataset
uspto-grants-2011_12
Patent number
US08071774B2

Reaction notes

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