Diisopropylethylamine → (4aS,10bR)-1,2,3,4,4a,5,6,10b-Octahydrobenzo[f]quinoline

HRID 1421891Notes

Reaction equation

HRID 1421891 reaction equation
ClC(OC(Cl)=O)C.C[N:9]1[C@@H:18]2[C@H:13]([C:14]3[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=3[CH2:16][CH2:17]2)[CH2:12][CH2:11][CH2:10]1.C(N(C(C)C)CC)(C)C>ClCCl.N>[CH2:12]1[C@H:13]2[C@H:18]([CH2:17][CH2:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=32)[NH:9][CH2:10][CH2:11]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 121360Benzo(f)quinoline, 1,2,3,4,4a,5,6,10b-octahydro-4-methyl-, trans-HCID 5213051-Chloroethyl chloroformate

Product 1

HCID 12327022(4aS,10bR)-1,2,3,4,4a,5,6,10b-Octahydrobenzo[f]quinolineYield 33%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 6344DichloromethaneSolvent

Procedure

1-Chloroethylchloroformate (2.01 ml, 18.61 mmol) was added with stirring to an ice-cooled solution of cis-and trans-4-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinoline (1.66 g, 8.34 mmol) in dichloromethane (60 ml). The mixture was allowed to warm to room temperature and stirred for a further 2 h. Diisopropylethylamine (2.2 ml, 12.6 mmol) was added and the mixture heated at reflux for 1 h. The mixture was cooled and concentrated in vacuo, dissolved in methanol and refluxed for 1 h. After cooling, the solvent was removed and the residue partitioned between saturated aqueous K2CO2 and dichloromethane (4×50 ml). The combined organic extracts were washed with water, dried (Na2SO4) and the solvent evaporated to afford an oil. Chromatography on silica using 10% methanol-ethyl acetate with 6.6 ml/L 0.880 ammonia as eluent gave the trans-isomer of the title compound (260 mg, 33%) as the first eluting product.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated in vacuo
  5. dissolutiondissolved in methanol
  6. temperaturerefluxed for 1 h
  7. temperatureAfter cooling
  8. customthe solvent was removed
  9. customthe residue partitioned between saturated aqueous K2CO2 and dichloromethane (4×50 ml)
  10. washThe combined organic extracts were washed with water
  11. dry with materialdried (Na2SO4)
  12. customthe solvent evaporated
  13. customto afford an oil

Sources & evidence

ORD record
ord-84bc117d0dc941b18a364dde7a7a685c
Source dataset
uspto-grants-2000_06
Patent number
US06080752

Reaction notes

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