Vinyl chloroformate → (+/-)-trans-4a-(3-Methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8, 8a-decahydroisoquinoline hydrochloride

HRID 2856

Reaction equation

HRID 2856 reaction equation
C([N:3]1[CH2:12][CH2:11][C@@:10]2([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)[C@@H:5]([CH2:6][CH2:7][C:8](=[O:21])[CH2:9]2)[CH2:4]1)C.CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.C(OC([Cl:43])=O)=C>ClCCCl>[ClH:43].[CH3:20][O:19][C:15]1[CH:14]=[C:13]([C@@:10]23[CH2:9][C:8](=[O:21])[CH2:7][CH2:6][C@H:5]2[CH2:4][NH:3][CH2:12][CH2:11]3)[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 78808Vinyl chloroformateHCID 88675Proton spongeHCID 10517409(+/-)-trans-1,2,3,4,4a,5,6,7,8,8a-Decahydro-2-ethyl-4a-(3-methoxyphenyl)-6-isoquinolinone

Product 1

HCID 86752321(+/-)-trans-4a-(3-Methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8, 8a-decahydroisoquinoline hydrochlorideYield 70.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 1.2 g (4.2 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline and 1.8 g (12.6 mmol) of proton sponge in 34 ml of 1,2-dichloroethane was treated with 1.4 ml (16.8 mmol) of vinylchloroformate at 0° C. under nitrogen atmosphere. The reaction mixture was stirred at this temperature for 15 min and then refluxed for 3 h, the solvent was removed in vacuo, the residue was taken up in water and extracted with Et2O. The organic layer was washed with 3% HCl, then was dried over Na2SO4 and the solvent was removed in vacuo. The dark residue was dissolved in EtOH, 3 ml of concentrated HCl were added and the solution refluxed for 3 hours. The solvent was removed in vacuo, obtaining 0.88 g of the title compound which was used as such in the subsequent step. M.p.=90° C. dec.

Workup

  1. temperaturerefluxed for 3 h
  2. customthe solvent was removed in vacuo
  3. extractionextracted with Et2O
  4. washThe organic layer was washed with 3% HCl
  5. dry with materialwas dried over Na2SO4
  6. customthe solvent was removed in vacuo
  7. dissolutionThe dark residue was dissolved in EtOH
  8. addition3 ml of concentrated HCl were added
  9. temperaturethe solution refluxed for 3 hours
  10. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-65c40f72159b46c38bd188c224445f20
Source dataset
uspto-grants-1998_03
Patent number
US05731322

Linked notes

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