2,6-Lutidine → HCID 70211003, compound

HRID 380536Notes

Reaction equation

HRID 380536 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([O:23][CH3:24])[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si](C(C)(C)C)(C)C)(=O)=O.[NH4+].[Cl-]>C(Cl)Cl>[CH3:24][O:23][CH:14]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 25517Ammonium ChlorideHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 53877270HCID 53877270, compound

Product 1

HCID 70211003HCID 70211003, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

410 mg (1.2 mmol) of 1-t-butoxycarbonyl-4-(methoxybenzyloxymethyl)piperidine and 0.28 mL (2.4 mmol) of 2,6-lutidine were combined in 2.5 mL of CH2Cl2. 0.42 mL (1.8 mmol) of t-butyldimethylsilyl trifluoromethane sulfonate were added and the mixture was stirred for 1 h at rt. 10 mL of sat'd NH4Cl-solution were added and the mixture was extracted with CH2Cl2. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was redissolved in 3 mL of THF. 2 mL of a solution of tetrabutylammonium fluoride (1M in THF) were added and the mixture was stirred for 2 h at rt. 10 mL of sat'd NaHCO3-solution were added and the mixture was extracted with CH2Cl2. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated to give the title compound which was used without further purification.

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. washThe combined organic fractions were washed with sat'd NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. dissolutionThe residue was redissolved in 3 mL of THF
  7. addition2 mL of a solution of tetrabutylammonium fluoride (1M in THF) were added
  8. stirringthe mixture was stirred for 2 h at rt
  9. addition10 mL of sat'd NaHCO3-solution were added
  10. extractionthe mixture was extracted with CH2Cl2
  11. washThe combined organic fractions were washed with sat'd NaCl solution
  12. dry with materialdried over MgSO4
  13. filtrationfiltered
  14. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c21fa7b4b22a4e0cb72d56d0b02e8ba8
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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