Trifluoroacetic acid → HCID 18364854, compound

HRID 380501Notes

Reaction equation

HRID 380501 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[OH:17])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:18]1([CH:16]([OH:17])[CH2:15][CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 18364778HCID 18364778, compound

Product 1

HCID 18364854HCID 18364854, compoundYield 117.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.48 g (4.66 mmol) of 1-t-butoxycarbonyl-4-(3-phenyl-3-hydroxypropyl)piperidine in 8 mL of CH2Cl2 at rt was added 2 mL of trifluoroacetic acid. After stirring for 2 h at rt, the reaction mixture was poured into 100 mL of sat'd NaHCO3 solution and extracted with CH2Cl2. The combined organic fractions were dried over MgSO4, filtered and the filtrate was concentrated to give 1.2 g of the title compound.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe combined organic fractions were dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f0ac9f1e24f747b386bf8e9fd1c552a6
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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