Formic Acid → (7aS,11aR)-2-[4-methoxy-2-(trifluoromethyl)phenyl]-10-methyl-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3',4':4,5]pyrrolo[3,2,1-ij]quinoline

HRID 1266107Notes

Reaction equation

HRID 1266107 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:16]4=[C:17]([C@@H:19]5[CH2:24][NH:23][CH2:22][CH2:21][C@@H:20]5[N:15]4[CH2:14][CH2:13][CH2:12]3)[CH:18]=2)=[C:5]([C:25]([F:28])([F:27])[F:26])[CH:4]=1.C=O.[CH:31](O)=O.[OH-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:16]4=[C:17]([C@@H:19]5[CH2:24][N:23]([CH3:31])[CH2:22][CH2:21][C@@H:20]5[N:15]4[CH2:14][CH2:13][CH2:12]3)[CH:18]=2)=[C:5]([C:25]([F:28])([F:26])[F:27])[CH:4]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 59012632HCID 59012632, compound

Product 1

HCID 69433356(7aS,11aR)-2-[4-methoxy-2-(trifluoromethyl)phenyl]-10-methyl-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3',4':4,5]pyrrolo[3,2,1-ij]quinolineYield 61.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The solution of (7aS,11aR)-2-[4-methoxy-2-(trifluoromethyl)phenyl]-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (30 mg, 0.077 mmol) in formaldehyde (37 wt % aqueous solution, 97 mg, 1.16 mmol) and formic acid (54 mg, 1.16 mmol) was heated at 80° C. for 2h. The reaction mixture was diluted with H2O then basified with 1N NaOH to pH 12 and extract with CHCl3. The combined organic solution was dried over MgSO4, concentrated in vacuo, and the residue was chromatographed (silica gel; CHCl3:MeOH 99:1-95:5) to give the title compound as a pale yellow oil (19 mg, 61%). MS (CI, NH3): 403.1 (base, M+H).

Workup

  1. extractionextract with CHCl3
  2. dry with materialThe combined organic solution was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customthe residue was chromatographed (silica gel; CHCl3:MeOH 99:1-95:5)

Sources & evidence

ORD record
ord-5880048591ef4fdba2abcc4ee04e0960
Source dataset
uspto-grants-2003_04
Patent number
US06548493B1

Reaction notes

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