Water → HCID 131718465, compound

HRID 1109126Notes

Reaction equation

HRID 1109126 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=O)[CH:8]2[CH2:13][C:14]([O:16]CC)=O.[CH3:20][CH:21]([CH3:25])[CH2:22][CH2:23][NH2:24].O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]2[CH2:5][CH2:6][C@H:7]3[C@H:8]([CH2:13][C:14](=[O:16])[N:24]3[CH2:23][CH2:22][CH:21]([CH3:25])[CH3:20])[C:9]=2[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7894IsoamylamineHCID 12541369HCID 12541369, compound

Product 1

HCID 131718465HCID 131718465, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.6 g (0.01755 mol) of ethyl 1,2,3,4-tetrahydro-5-methoxy-2-oxo-1-naphthylacetate were dissolved in 80 ml of toluene, 2.04 ml (0.01755 mol) of 3-methyl-butylamine were added thereto and the mixture was boiled for 24 hours on a water separator. After concentration the residue was hydro-genated with 1.8 g of Raney-nickel in 200 ml of ethanol at 120° and 140 bar for 10 hours. The material obtained was chromatographed over silica gel with cyclohexane/ethyl acetate 3:1. The product was dissolved in hot isopropyl ether and crystallized at room temperature. There were obtained 2.84 g (56%) of rac-cis-1,3,3a,4,5,9b-hexahydro-6-methoxy-3-(3-methyl-butyl)-2H-benzo[e]indol-2-one as white crystals with m.p. 81°-82° and 0.79 g (16%) of oily material from the mother liquors.

Workup

  1. concentrationAfter concentration the residue
  2. customwas hydro-genated with 1.8 g of Raney-nickel in 200 ml of ethanol at 120°
  3. customThe material obtained
  4. customwas chromatographed over silica gel with cyclohexane/ethyl acetate 3:1
  5. dissolutionThe product was dissolved in hot isopropyl ether
  6. customcrystallized at room temperature

Sources & evidence

ORD record
ord-d4feac91be08475f8240beee2b92d78d
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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