1-Chloroethyl chloroformate → HCID 70664459, compound

HRID 1026642Notes

Reaction equation

HRID 1026642 reaction equation
C([N:8]1[CH2:16][C@@H:15]2[C@@:10]([CH3:23])([C@@H:11]([CH3:22])[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.CC(Cl)OC(Cl)=O>C1(C)C=CC=CC=1.Cl.CO>[ClH:21].[Cl:21][C:20]1[C:13]2[CH2:12][C@H:11]([CH3:22])[C@:10]3([CH3:23])[C@@H:15]([CH2:16][NH:8][CH2:9]3)[C:14]=2[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 46909230HCID 46909230, compound

Product 1

HCID 70664459HCID 70664459, compoundYield 132.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
160 °C

Procedure

(3aR*,4S*,9bS*)-2-Benzyl-6-chloro-3a,4-dimethyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (0.153 mmol, 49.8 mg) was dissolved in toluene (1 ml). ACE-Cl (1.070 mmol, 0.118 ml, 153 mg) was added and the reaction mixture was heated in a microwave reactor at 160° C. for 15 minutes. Methanol (1 ml) was added and the reaction mixture was again heated in a microwave reactor at 160° C. for 5 minutes. The resulting solution was passed through an SCX cartridge and concentrated in vacuo to give a residue that was dissolved in 2 M HCl in MeOH and concentrated in vacuo to afford (3aR*,4S*,9bS*)-6-chloro-3a,4-dimethyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride (27.5 mg). m/z: 236.1 [M+H]+.

Workup

  1. temperaturethe reaction mixture was again heated in a microwave reactor at 160° C. for 5 minutes
  2. concentrationconcentrated in vacuo
  3. customto give a residue that
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e45b79dbada4e67808a0d65c1061924
Source dataset
uspto-grants-2014_05
Patent number
US08729274B2

Reaction notes

Loading…