Ethyl chloroformate → HCID 86740198, compound

HRID 371142Notes

Reaction equation

HRID 371142 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]23[CH:17]4[CH2:18][CH:14]([CH2:15][CH2:16]4)[CH:13]2[CH2:12][N:11](C)[CH2:10]3)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1(C)C=CC=CC=1.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]23[CH:17]4[CH2:18][CH:14]([CH2:15][CH2:16]4)[CH:13]2[CH2:12][N:11]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:10]3)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 10040193HCID 10040193, compound

Product 1

HCID 86740198HCID 86740198, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.0 g of 3a-(3,4-dichlorophenyl)octahydro-2-methyl-4,7-methano-1H-isoindole in 200 ml of toluene was added, dropwise over a 30 minute period, at room temperature, 30 ml of a solution of freshly distilled ethyl chloroformate in toluene. The reaction mixture was heated under reflux for 16 hours, then was concentrated in vacuo to give a colorless, viscous liquid. This liquid was dissolved in dichloromethane and chromatographed by preparative liquid chromatography on a silica gel column, eluting with 10% ethyl acetate/hexane and gave 1.9 g of 3a-(3,4-dichlorophenyl)octahydro-4,7-methano-2H-isoindole-2-carboxylic acid, ethyl ester as a slightly yellow, viscous liquid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 16 hours
  3. concentrationwas concentrated in vacuo
  4. customto give a colorless, viscous liquid
  5. customchromatographed by preparative liquid chromatography on a silica gel column
  6. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-f7a4b61127714ab4a5ed81d7ebac8609
Source dataset
uspto-grants-1985_07
Patent number
US04529736

Reaction notes

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