Trifluoroacetic acid → HCID 44467324, compound

HRID 418557Notes

Reaction equation

HRID 418557 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([N:21]([C:33]2[CH:34]=[C:35]3[C:39](=[CH:40][CH:41]=2)[NH:38][CH:37]=[CH:36]3)[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29](OC)=[O:30])[CH:24]=2)[CH2:17][CH2:16]1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(Cl)Cl>[NH:38]1[C:39]2[C:35](=[CH:34][C:33]([N:21]([CH2:22][C:23]3[CH:24]=[C:25]([CH2:29][OH:30])[CH:26]=[CH:27][CH:28]=3)[CH:18]3[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]3)=[CH:41][CH:40]=2)[CH:36]=[CH:37]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21226445Aluminium lithium hydrideHCID 66650431HCID 66650431, compound

Product 1

HCID 44467324HCID 44467324, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 mL) was added to a solution of 4-[(1H-indol-5-yl)-(3-methoxycarbonyl-benzyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (210 mg, 0.453 mmol) in DCM (2.0 mL). The reaction mixture was stirred for 3 hours, the solvent was then evaporated under reduced pressure and the residue was dissolved in DCM, a mixture of MeOH/NH4OH (9.5/0.5) was then added. The resulting mixture was filtered through a celite and silica pad and the filtrate was evaporated under reduced pressure. The residue was dissolved in THF (5.0 mL) and a solution of lithium aluminum hydride (1.0 M in THF, 1.81 mL, 1.81 mmol) was added under nitrogen atmosphere. The reaction mixture was stirred for 30 minutes and it was then quenched by addition of Na2SO4.10H2O. The resulting mixture was filtered and the filtrate was evaporated under reduced pressure to give 13.2 mg (9% yield) of (3-{[(1H-indol-5-yl)-piperidin-4-yl-amino]-methyl}-phenyl)-methanol, MS=336 [M+H]+.

Workup

  1. customthe solvent was then evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in DCM
  3. additiona mixture of MeOH/NH4OH (9.5/0.5)
  4. additionwas then added
  5. filtrationThe resulting mixture was filtered through a celite and silica pad
  6. customthe filtrate was evaporated under reduced pressure
  7. dissolutionThe residue was dissolved in THF (5.0 mL)
  8. stirringThe reaction mixture was stirred for 30 minutes
  9. customit was then quenched by addition of Na2SO4.10H2O
  10. filtrationThe resulting mixture was filtered
  11. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6417df2e5ec6426fa075e0682abb8e54
Source dataset
uspto-grants-2012_01
Patent number
US08093285B2

Reaction notes

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