Hydrochloric Acid → (+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-yl ethylcarbamate hydro-chloride

HRID 1109229노트

반응식

HRID 1109229 반응식
[CH:1]1([CH2:7][CH2:8][N:9]2[C@@H:17]3[C@@H:12]([C:13]4[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[C:14]=4[CH2:15][CH2:16]3)[CH2:11][CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:30]([N:32]=[C:33]=[O:34])[CH3:31].C(=O)([O-])O.[Na+].[ClH:40]>C(#N)C.C(O)C>[ClH:40].[CH2:30]([NH:32][C:33](=[O:34])[O:22][C:18]1[C:14]2[CH2:15][CH2:16][C@H:17]3[C@H:12]([CH2:11][CH2:10][N:9]3[CH2:8][CH2:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:13]=2[CH:21]=[CH:20][CH:19]=1)[CH3:31]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 86747896(+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol

생성물 1

HCID 86747897(+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-yl ethylcarbamate hydro-chloride수율 51%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6342Acetonitrile용매

실험 절차

A suspension of 2.00 g (0.0067 mol) of (+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol in 100 ml of acetonitrile was treated with 1.9 ml (0.013 mol) of triethylamine and 2.1 ml (0.027 mol) of ethyl isocyanate. The mixture was boiled under reflex for 20 hours and then poured into aqueous sodium hydrogen carbonate solution, whereupon the mixture was extracted with methylene chloride. After drying the organic phase with sodium sulphate and distillation of the solvent the residue was chromatographed over silica gel with methylene chloride/methanol 20:1. The oil obtained was dissolved in ethanol and treated with an equimolar amount of ethanolic HCl. After concentration the residue was dissolved in methylene chloride, treated with active charcoal and sodium sulphate, filtered and the solvent was distilled off in a vacuum. The residue was suspended in ethyl acetate, filtered off and dried in a vacuum. There were obtained 1.39 g (51%) of (+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-yl ethylcarbamate hydro-chloride with m.p. 133°-136°.

후처리

  1. extractionwas extracted with methylene chloride
  2. customAfter drying the organic phase
  3. distillationwith sodium sulphate and distillation of the solvent the residue
  4. customwas chromatographed over silica gel with methylene chloride/methanol 20:1
  5. customThe oil obtained
  6. concentrationAfter concentration the residue
  7. dissolutionwas dissolved in methylene chloride
  8. additiontreated with active charcoal and sodium sulphate
  9. filtrationfiltered
  10. distillationthe solvent was distilled off in a vacuum
  11. filtrationfiltered off
  12. customdried in a vacuum

출처 및 근거

ORD 기록
ord-ab3ed7180e4b4f5d992352ecab2eb18b
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05318967

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