Water → HCID 131718472, compound

HRID 1109133Notes

Reaction equation

HRID 1109133 reaction equation
[CH2:1]([N:9]1[C@@H:17]2[C@@H:12]([C:13]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[C:14]=3[CH2:15][CH2:16]2)[CH2:11][CH2:10]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:23]([N:25]([CH2:28]C)[CH2:26]C)C.CC(N(C)Cl)=[O:32].O>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:23][N:25]([CH3:28])[C:26](=[O:32])[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[CH2:1][CH2:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:13]=2[CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12663100HCID 12663100, compoundHCID 131718471HCID 131718471, compound

Product 1

HCID 131718472HCID 131718472, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

2.69 g (0.00917 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-3-phenethyl-1H-benzo[e]indol-6-ol were dissolved in 90 ml of toluene. 0.974 g (1.34 ml, 0.00963 mol) of triethylamine and 112 mg (917 mmol, 0.1 eq.) of 4-dimethylaminopyridine were added thereto in succession and then 0.88 ml (0.00963 mol) of dimethyl chloroformamide were added dropwise thereto. The mixture was boiled under reflux for 5 hours, then cooled, poured into water and extracted with CH2Cl2. The organic phase was washed with saturated aqueous NaHCO3 and NaCl solutions, dried with Na2SO4, filtered and concentrated. By chromatography of the residue over silica gel with dichloromethane/isopropyl alcohol and crystallization of the product in hexane/ethyl acetate there were obtained 3.08 g (92%) of rac-cis-2,3,3a,4,5,9b-hexa-hydro-3-phenethyl-1H-benzo[e]indol-6-yl dimethylcarbamate as yellowish crystals with m.p. 98°-102°.

Workup

  1. temperatureunder reflux for 5 hours
  2. temperaturecooled
  3. extractionextracted with CH2Cl2
  4. washThe organic phase was washed with saturated aqueous NaHCO3 and NaCl solutions
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customBy chromatography of the residue over silica gel with dichloromethane/isopropyl alcohol and crystallization of the product in hexane/ethyl acetate there

Sources & evidence

ORD record
ord-1da00c32a6bc4e12bbbd291351785930
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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