Potassium Carbonate → methyl (2S,5R)-5-(phenylmethoxyamino)piperidine-2-carboxylate

HRID 710962Notes

Reaction equation

HRID 710962 reaction equation
Cl.Cl.[CH2:3]([O:10][NH:11][C@H:12]1[CH2:17][NH:16][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:13]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH2:3]([O:10][NH:11][C@H:12]1[CH2:17][NH:16][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:13]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 122530207Methyl(2S,5R)-5-(benzyloxyamino)piperidine-2-carboxylate dihydrochloride

Product 1

HCID 71722743methyl (2S,5R)-5-(phenylmethoxyamino)piperidine-2-carboxylateYield 94.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To (2S,5R)-methyl 5-(benzyloxyamino)piperidine-2-carboxylate, dihydrochloride (1.319 g) were added ethyl acetate (20 mL) and 50% potassium carbonate aqueous solution (20 mL) for liquid separation and the aqueous layer was extracted with ethyl acetate (15 mL) three times. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered, subsequently concentrated under reduced pressure, and dried under vacuum overnight to afford 975 mg of the title compound (yield 94%).

Workup

  1. customfor liquid separation
  2. extractionthe aqueous layer was extracted with ethyl acetate (15 mL) three times
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationsubsequently concentrated under reduced pressure
  7. customdried under vacuum overnight

Sources & evidence

ORD record
ord-c38d65496c1745ce9dd03e727a9476f0
Source dataset
uspto-grants-2015_11
Patent number
US09181250B2

Reaction notes

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