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

HRID 1109155
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HRID 1109155 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.[CH3:30][N:31]=[C:32]=[O:33].C(=O)([O-])O.[Na+].[ClH:39]>C(#N)C.C(O)C>[ClH:39].[CH3:30][NH:31][C:32](=[O:33])[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
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참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 516892Sodium BicarbonateHCID 86747896(+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol

생성물 1

HCID 86747894(+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-yl methylcarbamate hydrochloride
수율 60%

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 1.6 ml (0.027 mol) of methyl isocyanate. The mixture was boiled under reflux for 5 hours and the 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. The residue was suspended in ethyl acetate, filtered off and dried in a vacuum. There were obtained 1.58 g (60%) of (+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-yl methylcarbamate hydrochloride with m.p. 209°-212°.

후처리

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

출처 및 근거

ORD 기록
ord-1c40e65805344acaaa2b23dd56d04ac2
출처 데이터셋
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05318966

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