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

HRID 1109157
ノート
印刷プレビュー

反応式

HRID 1109157 の反応式
[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:34]=[C:35]=[O:36])[CH2:31][CH2:32][CH3:33].C(=O)([O-])O.[Na+].[ClH:42]>C(#N)C.CO>[ClH:42].[CH2:30]([NH:34][C:35](=[O:36])[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)[CH2:31][CH2:32][CH3:33]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 8110Butyl isocyanateHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 86747896(+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol

生成物 1

HCID 131718499rac-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-yl butylcarbamate hydrochloride
収率 38%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒

実験手順

A suspension of 2.00 g (0.0067 mol) of rac-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 3.0 ml (0.027 mol) of butyl isocyanate. The mixture was boiled under reflux 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 methanol and treated with an equimolar amount of ethanolic HCl. After drying with sodium sulphate, concentration to a volume of about 30 ml and filtration there were obtained 1.11 g (38%) of rac-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-yl butylcarbamate hydrochloride with m.p. 192°-194°.

後処理

  1. temperatureunder reflux for 20 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. dry with materialAfter drying with sodium sulphate, concentration to a volume of about 30 ml
  8. filtrationfiltration there

出典と根拠

ORDレコード
ord-1d1dc0deefe7431db1c623e467c03548
出典データセット
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05318966

反応ノート

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