Trifluoroacetic acid → 2-Benzyl-5-methoxy-2,3,3a,8a-tetrahydro-1H-2-aza-cyclopenta[a]inden-8-one

HRID 508491Notes

Reaction equation

HRID 508491 reaction equation
CO[CH2:3][N:4]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][Si](C)(C)C.C(O)(C(F)(F)F)=O.[CH3:24][O:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[C:31](=[O:35])[CH:30]=[CH:29]2>C(Cl)Cl>[CH2:10]([N:4]1[CH2:3][CH:29]2[C:28]3[CH:27]=[C:26]([O:25][CH3:24])[CH:34]=[CH:33][C:32]=3[C:31](=[O:35])[CH:30]2[CH2:5]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 110409905-Methoxy-1H-inden-1-one

Product 1

HCID 672034582-Benzyl-5-methoxy-2,3,3a,8a-tetrahydro-1H-2-aza-cyclopenta[a]inden-8-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (17.3 mL, 67.6 mmol) and TFA (3.4 mL) were added to a solution of 5-methoxy-inden-1-one (5.4 g, 33.8 mmol) in CH2Cl2 (165 mL) at 0° C. The reaction was stirred for 3 hours at room temperature and quenched with saturated aqueous NaHCO3 (165 mL). The organic layer was separated, washed with brine (100 mL), dried over MgSO4, and concentrated to afford the subtitle compound, which was used without further purification. MS calculated for C19H19NO2+H: 294, observed: 294.

Workup

  1. customquenched with saturated aqueous NaHCO3 (165 mL)
  2. customThe organic layer was separated
  3. washwashed with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c2f48cfd2e854b7893445211ac1da838
Source dataset
uspto-grants-2015_08
Patent number
US09096520B2

Reaction notes

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