Trifluoroacetic acid → HCID 21955150, compound

HRID 747010Notes

Reaction equation

HRID 747010 reaction equation
FC(F)(F)C(O)=O.O[C:9]1([CH2:22][CH2:23][C:24]([OH:27])([CH3:26])[CH3:25])[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]1>ClCCl>[CH3:26][C:24]1([CH3:25])[CH2:23][CH2:22][C:9]2([CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)[O:27]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21955185HCID 21955185, compound

Product 1

HCID 21955150HCID 21955150, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (10 ml) was added to a solution of 1,1-dimethylethyl 4-hydroxy-4-(3-hydroxy-3-methylbut-1-yl)-1-piperidinecarboxylate (from step (iv) above; 3.9 g, 13.57 mmol) in dichloromethane (10 ml) and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2/MeOH/NH3(Aq.) (90:10:1) to give the title compound (2.04 g, 89%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by flash column chromatography on silica gel
  3. washeluting with CH2Cl2/MeOH/NH3(Aq.) (90:10:1)

Sources & evidence

ORD record
ord-f2d4d37e11704ced8f808483a278fef5
Source dataset
uspto-grants-2008_07
Patent number
US07393858B2

Reaction notes

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