Water → HCID 131718468, compound

HRID 1109129Notes

Reaction equation

HRID 1109129 reaction equation
[CH3:1][CH:2]([CH3:19])[CH2:3][CH2:4][N:5]1[C@@H:13]2[C@@H:8]([C:9]3[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[C:10]=3[CH2:11][CH2:12]2)[CH2:7][CH2:6]1.[CH2:20]([N:22]([CH2:25]C)[CH2:23]C)C.CC(N(C)Cl)=[O:29].O>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:20][N:22]([CH3:25])[C:23](=[O:29])[O:18][C:14]1[C:10]2[CH2:11][CH2:12][C@H:13]3[C@H:8]([CH2:7][CH2:6][N:5]3[CH2:4][CH2:3][CH:2]([CH3:19])[CH3:1])[C:9]=2[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12663100HCID 12663100, compoundHCID 131718467HCID 131718467, compound

Product 1

HCID 131718468HCID 131718468, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

2.71 g (0.01045 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-3-(3-methyl-butyl)-1H-benzo[e]indol-6-ol were dissolved in 60 ml of toluene. 2.1 g (2.90 ml, 0.0208 mol) of triethylamine and 128 mg (1045 mmol, 0.1 eq.) of 4-dimethylaminopyridine were added thereto in succession and then 1.92 ml (0.02088 mol) of dimethyl chloroformamide were added dropwise thereto. The mixture was boiled under reflux for 2 hours, then cooled, poured into water and extracted with toluene. The organic phase was washed with water, dried with Na2SO4, filtered and concentrated. By chromatography of the residue over silica gel with ethyl acetate there were obtained 2.91 g (84%) of oily rac-cis-2,3,3a, 4,5,9b-hexahydro-3-(3-methyl-butyl)-1H-benzo[e]indol-6-yl dimethylcarbamate.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperaturecooled
  3. extractionextracted with toluene
  4. washThe organic phase was washed with water
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-57c3ff7d9dc44d4c862e91a55250e300
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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