Sodium Carbonate → 5-(4'-(1-(Methoxyamino)ethyl)-2'-methylbiphenyl-4-carbonyl)-1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]

HRID 1741100Notes

Reaction equation

HRID 1741100 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].CC(C)([O-])C.[K+].[C:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([N:28]3[C:36]4[CH:35]=[C:34]5[C:37]6([CH2:44][O:45][C:33]5=[CH:32][C:31]=4[CH2:30][CH2:29]3)[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]6)=[O:27])=[CH:22][CH:21]=2)=[C:16]([CH3:46])[CH:15]=1)(=O)[CH3:12].C([O-])([O-])=O.[Na+].[Na+]>CO>[CH3:3][O:2][NH:4][CH:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([N:28]3[C:36]4[CH:35]=[C:34]5[C:37]6([CH2:44][O:45][C:33]5=[CH:32][C:31]=4[CH2:30][CH2:29]3)[CH2:38][CH2:39][N:40]([CH3:43])[CH2:41][CH2:42]6)=[O:27])=[CH:22][CH:21]=2)=[C:16]([CH3:46])[CH:15]=1)[CH3:12]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 218337795-(4'-Acetyl-2'-methylbiphenyl-4-carbonyl)-1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]HCID 23665647Potassium tert-butoxide

Product 1

HCID 218338545-(4'-(1-(Methoxyamino)ethyl)-2'-methylbiphenyl-4-carbonyl)-1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]Yield 104.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methoxylamine hydrochloride (0.06 g, 0.7 mmol) was added to a stirred solution of potassium t-butoxide (0.06 g, 0.5 mmol) in methanol (10 ml) under argon. After 20 minutes at room temperature, the solution was treated with a solution of 5-(4'-acetyl-2'-methylbiphenyl-4-carbonyl)-1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (E10, 0.16 g, 0.3 mmole) in methanol (10 ml) and stirred at room temperature for 18 hours, followed by 1 hour heating under reflux. The solution was allowed to cool, treated with 10% Na2CO3 solution (40 ml) and extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated in vacuo to afford the title compound as a yellow solid (0.16 g, 94%).

Workup

  1. waitfollowed by 1 hour
  2. temperatureheating
  3. temperatureunder reflux
  4. temperatureto cool
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9af2d328e53e488cae3cd3c346dc80dd
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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