Trifluoroacetic acid → HCID 58010683, compound

HRID 2062298Notes

Reaction equation

HRID 2062298 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6](=[O:22])[NH:7][CH2:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]1.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6](=[O:22])[NH:7][CH2:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 58010986HCID 58010986, compound

Product 1

HCID 58010683HCID 58010683, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-methoxyethyl((S)-1-(tert-butoxycarbonyl)piperidin-3-yl)methylcarbamate (496 mg, 1.6 mmol) dissolved in 10 mL CH2Cl2 was added 5 mL TFA, and the reaction was stirred for 1 hour. After neutralizing the mixture with a 1 N NaOH solution it was extracted with CH2Cl2, and the combined organic layers were dried over MgSO4, filtered, and concentrated to give 2-methoxyethyl((R)-piperidin-3-yl)methylcarbamate (300 mg, 87%) which was used without further purification. LC/MS: m/z 217.5 (M+H)+ at 0.49 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. extractionwas extracted with CH2Cl2
  2. dry with materialthe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3007dafa9fb8466684f5764ccd166b44
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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