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

HRID 1109158Notes

Reaction equation

HRID 1109158 reaction equation
[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]

Participants

9

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-467495bc51854b6788cd03d0e41c6aff
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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