Sulfuric Acid → HCID 15147196, compound

HRID 380494Notes

Reaction equation

HRID 380494 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.OS(O)(=O)=O>O>[F:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][O:15][CH2:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 18364794123855-52-7

Product 1

HCID 15147196HCID 15147196, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 0.89 g (2.35 mmol) of 1-t-butoxycarbonyl-4-(4-fluorobenzyloxymethyl)piperidine in 8 mL of H2O at rt was added 2 mL of TFA and the reaction mixture was stirred for 2 h. To the reaction mixture was added 50 mL of 0.5N H2SO4. After stirring vigorously for 5 min, the mixture was was washed with CH2Cl2. The aqueous fraction was made basic with solid K2CO3 and extracted with CH2Cl2. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4 and filtered. The filtrate was concentrated to give the title compound.

Workup

  1. stirringAfter stirring vigorously for 5 min
  2. washthe mixture was was washed with CH2Cl2
  3. extractionextracted with CH2Cl2
  4. washThe combined organic fractions were washed with sat'd NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d451e90670114232bde467b089f4d0e0
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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