Carbonate Ion → Methyl 4-amino-1-benzylpiperidine-3-carboxylate

HRID 2225062Notes

Reaction equation

HRID 2225062 reaction equation
Cl.[CH3:2][O:3][C:4]([CH:6]1[C:11](=O)[CH2:10][CH2:9][N:8]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7]1)=[O:5].C(=O)([O-])[O-].C([O-])(=O)C.[NH4+].C([BH3-])#[N:30].[Na+]>CO.O>[CH3:2][O:3][C:4]([CH:6]1[CH:11]([NH2:30])[CH2:10][CH2:9][N:8]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7]1)=[O:5]

Participants

7

Reactant 4

HCID 19660Carbonate IonHCID 107479Methyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochlorideHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 59656328Methyl 4-amino-1-benzylpiperidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a 25° C. solution of 1-benzyl-4-oxo-piperidine-3-carboxylic acid methyl ester hydrochloride (2.97 g, 10 mmol) in MeOH (10 mL) was added MP-Carbonate (12 g, 30 mmol, 2.54 mmol/g). After shaking at 25° C. for 1 h, the solution was filtered. To the resultant solution was added ammonium acetate (7.71 g, 100 mmol). After stirring at 65° C. overnight, sodium cyanoborohydride (610 mg, 10 mmol) was added into the resultant mixture and the mixture further stirred for 2 h at 50° C. The solution was then concentrated in vacuo to give a solid. The resultant solid was dissolved in water (100 mL) and the aqueous layer was extracted with CH2Cl2. The organic extracts were combined, washed with brine and dried over MgSO4. The solution was filtered and concentrated in vacuo to give the crude product 4-amino-1-benzyl-piperidine-3-carboxylic acid methyl ester (6) as a mixture of diastereomers. LCMS showed m/z: 249 (M+H)+. This material was used without further purification.

Workup

  1. filtrationthe solution was filtered
  2. stirringAfter stirring at 65° C. overnight
  3. stirringthe mixture further stirred for 2 h at 50° C
  4. concentrationThe solution was then concentrated in vacuo
  5. customto give a solid
  6. extractionthe aqueous layer was extracted with CH2Cl2
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. filtrationThe solution was filtered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4e4dd4d4fc9948f6aab696c484989584
Source dataset
uspto-grants-2008_05
Patent number
US07378525B2

Reaction notes

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