Ethyl chloroformate → HCID 131731400, compound

HRID 1026647Notes

Reaction equation

HRID 1026647 reaction equation
C([N:8]1[CH2:16][C@H:15]2[C@:10]([CH3:22])([CH2:11][CH2:12][C:13]3[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:14]=32)[CH2:9]1)C1C=CC=CC=1.[C:23](Cl)(=[O:27])[O:24][CH2:25][CH3:26]>C1(C)C=CC=CC=1>[Cl:21][C:20]1[C:13]2[CH2:12][CH2:11][C@@:10]3([CH3:22])[C@H:15]([CH2:16][N:8]([C:23]([O:24][CH2:25][CH3:26])=[O:27])[CH2:9]3)[C:14]=2[CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 70664621HCID 70664621, compound

Product 1

HCID 131731400HCID 131731400, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

cis-2-Benzyl-6-chloro-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (18.60 mmol, 5.8 g) was dissolved in toluene and heated to reflux. Ethyl carbonochloridate (55.8 mmol, 5.33 ml, 6.06 g) was added dropwise and the reaction mixture left to stir at reflux for 2 hours. TLC and mass spec showed no starting material. Solvent removed in vacuo and crude material purified by silica column chromatography (eluting with 0-30% ethyl acetate:heptane) to give cis-ethyl 6-chloro-3a-methyl-3,3a,4,5-tetrahydro-1H-benzo[e]isoindole-2(9bH)-carboxylate (4.89 g), m/z=294.3 [M+H]+.

Workup

  1. temperatureheated to reflux
  2. waitthe reaction mixture left
  3. temperatureat reflux for 2 hours
  4. customSolvent removed in vacuo and crude material
  5. custompurified by silica column chromatography (eluting with 0-30% ethyl acetate:heptane)

Sources & evidence

ORD record
ord-3f3255842ff4472796cd68fca12e0387
Source dataset
uspto-grants-2014_05
Patent number
US08729274B2

Reaction notes

Loading…