Potassium Carbonate → cis-7-Methoxy-4-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinoline

HRID 1421900Notes

Reaction equation

HRID 1421900 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][O:16][C:17]1[C:30]2[CH2:29][CH2:28][C@H:27]3[C@H:22]([CH2:23][CH2:24][CH2:25][NH:26]3)[C:21]=2[CH:20]=[CH:19][CH:18]=1.[C:31]1([C:37]2[CH:50]=[CH:49][C:40]([C:41]([NH:43][CH2:44][CH2:45][CH2:46][CH:47]=O)=[O:42])=[CH:39][CH:38]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C([O-])([O-])=O.[K+].[K+]>ClC(Cl)C.C(OCC)(=O)C.CCCCC>[CH3:15][O:16][C:17]1[C:30]2[CH2:29][CH2:28][C@H:27]3[C@H:22]([CH2:23][CH2:24][CH2:25][N:26]3[CH2:47][CH2:46][CH2:45][CH2:44][NH:43][C:41](=[O:42])[C:40]3[CH:49]=[CH:50][C:37]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:38][CH:39]=3)[C:21]=2[CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 217125654-(4-Phenylbenzoylamino)butyraldehydeHCID 86654085cis-7-Methoxy-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinoline

Product 1

HCID 86755478cis-7-Methoxy-4-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolineYield 60%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 22335286Ethyl acetate pentaneSolvent

Procedure

Sodium triacetoxyborohydride (1.5 g, 6.9 mmol) was added to a stirred mixture of cis-7-methoxy-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinoline (D6b, 1.0 g, 4.6 mmol) and 4-(4-phenylbenzoylamino)butyraldehyde (1.4 g, 5.1 mmol) in dichloroethane (50 ml) at room temperature. After stirring for 12 h, saturated aqueous K2CO3 (40 ml) was added and the mixture extracted into dichloromethane (3×20 ml). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo to give a gum. Chromatography on silica, using 50-100% ethyl acetate/pentane as elution gradient, gave the title compound as a white solid (1.29 g, 60%).

Workup

  1. extractionthe mixture extracted into dichloromethane (3×20 ml)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give a gum
  6. washas elution gradient

Sources & evidence

ORD record
ord-a95aab9ba6844463b0c4f4828b7d3176
Source dataset
uspto-grants-2000_06
Patent number
US06080752

Reaction notes

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