Methanol → HCID 70664979, compound

HRID 1026628Notes

Reaction equation

HRID 1026628 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.ClC(OC(Cl)C)=O.CO>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][NH:8][CH2:9]3)[C:14]=2[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 70664621HCID 70664621, compound

Product 1

HCID 70664979HCID 70664979, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of cis-2-benzyl-6-chloro-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (0.882 mmol, 0.275 g) in toluene (2 ml) was added 1-chloroethyl chloroformate (6.17 mmol, 0.883 g) and the reaction mixture was heated at 160° C. for 15 min in a microwave reactor. MeOH (2 ml) was added and the mixture further irradiated at 160° C. for 5 mins. The mixture was concentrated in vacuo and then diluted with water and extracted with DCM (3×). The combined organics were dried over Na2SO4 and concentrated in vacuo to afford a residue that was purified by silica column chromatography (eluting with DCM—20% MeOH in DCM) to afford cis-6-chloro-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (163 mg), m/z=222.0 [M+H]+.

Workup

  1. customthe mixture further irradiated at 160° C. for 5 mins
  2. concentrationThe mixture was concentrated in vacuo
  3. additiondiluted with water
  4. extractionextracted with DCM (3×)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto afford a residue that
  8. customwas purified by silica column chromatography (eluting with DCM—20% MeOH in DCM)

Sources & evidence

ORD record
ord-a3bf15832fc94bcbadef2543ee941f6c
Source dataset
uspto-grants-2014_05
Patent number
US08729274B2

Reaction notes

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