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

HRID 1109231노트

반응식

HRID 1109231 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.[CH2:23]([N:25]([CH2:28]C)[CH2:26]C)[CH3:24].C(C(N(C)[Cl:35])=[O:33])C.C(=O)([O-])O.[Na+].Cl>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[ClH:35].[CH2:23]([N:25]([CH3:28])[C:26](=[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)[CH3:24]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 86747896(+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-olHCID 86747901Ethylmethyl chloroformamide

생성물 1

HCID 86747899(+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-yl ethylmethylcarbamate hydrochloride수율 882.7%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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 toluene was treated with 1.1 ml (0.008 mol) of triethyl-amine, 1.00 g (0.008 mol) of 4-dimethylaminopyridine and 1.00 g (0.008 mol) of ethylmethyl chloroformamide. The mixture was boiled under reflux for 4 hours and then poured into aqueous sodium hydrogen carbonate solution and 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 ethyl acetate and treated with an equimolar amount of ethanolic HCl. After drying with sodium sulphate, concentration to a volume of about 25 ml and filtration there were obtained 24.9 g (88%) of (+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-yl ethylmethylcarbamate hydrochloride with m.p. 181°-184°.

후처리

  1. temperatureunder reflux for 4 hours
  2. extractionextracted 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. dry with materialAfter drying with sodium sulphate, concentration to a volume of about 25 ml
  8. filtrationfiltration there

출처 및 근거

ORD 기록
ord-f309201381c2491981c2804199e2a89d
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05318967

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