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

HRID 1421899Notes

Reaction equation

HRID 1421899 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+]>ClCCl>[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

6

Reactant 4

HCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 13611558trans-7-Methoxy-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolineHCID 217125654-(4-Phenylbenzoylamino)butyraldehyde

Product 1

HCID 54493650trans-7-Methoxy-4-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride 0.83 g, 3.9 mmol) was added to a stirred mixture of trans-7-methoxy-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinoline (D6a, 0.57 g, 2.6 mmol) and 4-(4-phenylbenzoylamino)butyraldehyde (0.77 g, 2.9 mmol) in dichloromethane (50 ml) at room temperature. After stirring for 6 h, the mixture was poured onto saturated aqueous K2CO3 (40 ml) and extracted with dichloromethane (3×20 ml). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo to afford a white solid which was chromatographed on silica using 40-100% ethyl acetate/pentane as elution gradient. The title compound was obtained as a white solid (1.2 g, 99%).

Workup

  1. extractionextracted with dichloromethane (3×20 ml)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto afford a white solid which
  6. customwas chromatographed on silica using 40-100% ethyl acetate/pentane as elution gradient

Sources & evidence

ORD record
ord-3a96c2b8e8a846ac8b4350abf212a84d
Source dataset
uspto-grants-2000_06
Patent number
US06080752

Reaction notes

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