Trifluoroacetic acid → HCID 69698040, compound

HRID 412617Notes

Reaction equation

HRID 412617 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:21]([O:23][CH2:24][CH3:25])=[O:22])([CH2:14][CH2:15][CH:16]2[O:20][CH2:19][CH2:18][O:17]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH2:24]([O:23][C:21]([C:11]1([CH2:14][CH2:15][CH:16]2[O:17][CH2:18][CH2:19][O:20]2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:22])[CH3:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 60064213HCID 60064213, compound

Product 1

HCID 69698040HCID 69698040, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-ethoxycarbonyl-4-[2-(1,3-dioxolan-2-yl)ethyl]piperidine-1-carboxylic acid tert-butyl ester (450 mg) in chloroform (2 ml) was added trifluoroacetic acid (2 ml), and the mixture was stirred for several minutes. After completion of the reaction, the solvent was evaporated and to the obtained residue was added aqueous sodium hydrogencarbonate solution. The mixture was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated to give 4-[2-(1,3-dioxolan-2-yl)ethyl]piperidine-4-carboxylic acid ethyl ester. Then, in the same manner as in Example 10, Step 1, the title compound (460 mg) was obtained from sodium hydrogencarbonate (127 mg) and benzyloxycarbonyl chloride (0.22 ml).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated and to the obtained residue
  3. additionwas added aqueous sodium hydrogencarbonate solution
  4. extractionThe mixture was extracted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-db2bfbad7ab54694a4934a8cfd0f09e0
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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