Acetic Acid → HCID 131718503, compound

HRID 1109161Notes

Reaction equation

HRID 1109161 reaction equation
[CH2:1]1[C@H:9]2[C@H:4]([CH2:5][CH2:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)[N:3]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[C:23](=O)[C:22]3=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]3[C:20]2=[O:29])[CH2:2]1.[H][H].[C:32](O)(=[O:34])C>[Pd]>[CH3:32][O:34][C:13]1[C:7]2[CH2:6][CH2:5][C@H:4]3[C@H:9]([CH2:1][CH2:2][N:3]3[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]3[CH2:23][C:22]4[C:21](=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:20]3=[O:29])[C:8]=2[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 131718504HCID 131718504, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131718503HCID 131718503, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 3.10 g (0.007 mol) of rac-N-[5-(cis-1,2,3a, 4,5,9b-hexahydro-3H-benzo[e]indol-3-yl)pentyl]phthalimide in 100 ml of glacial acetic acid was treated with 1.0 g of 10% palladium/charcoal and hydrogenated at 60° for 6 hours at 20 bar hydrogen pressure. The acetic acid was distilled off and the residue was taken up in methylene chloride. The solution was washed with 2N sodium hydroxide solution, dried with sodium sulphate and concentrated. Chromatography over silica gel with ethyl acetate/methanol 19:1 yielded 0.80 g (27%) of rac-cis-2-[5-(6-methoxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-3-yl)pentyl]isoindolin-1-one as a yellow oil [MS: m/e (% basis peak)=404 (M+, 6), 216 (100), 202 (8), 185 (6), 146 (7)] as well as 1.64 g (55%) of rac-2-[5-(6-methoxy-2,3,3a,4,5,9b-hexahydro-1H-cis-benzo[e]indol-6-yl)pentyl]octahydro-cis-isoindole-1,3-dione as a yellow oil [MS: m/e (% basis peak)=424 (M+ , 7), 216 (100), 185 (5)].

Workup

  1. distillationThe acetic acid was distilled off
  2. washThe solution was washed with 2N sodium hydroxide solution
  3. dry with materialdried with sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8f16858e83ac4a63a2b9c4964b10c444
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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