Trifluoroacetic acid → Ethyl 4-amino-1-benzylpiperidine-3-carboxylate

HRID 2245351Notes

Reaction equation

HRID 2245351 reaction equation
[CH3:1]OC(C1C(N)N(CC2C=CC=CC=2)CCC=1)=O.[OH-].[Na+].[CH3:21][O:22][C:23]([C:25]1[CH2:26][N:27]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:28][CH2:29][C:30]=1[NH2:31])=[O:24].C(O)(C(F)(F)F)=O.[BH4-].[Na+].[NH4+].[Cl-]>C(O)C.C1COCC1>[CH2:21]([O:22][C:23]([CH:25]1[CH:30]([NH2:31])[CH2:29][CH2:28][N:27]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:26]1)=[O:24])[CH3:1]

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 563385Methyl 4-amino-1-benzyl-1,2,5,6-tetrahydropyridine-3-carboxylateHCID 4311764Sodium borohydrideHCID 68687101Amino-1-benzyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester

Product 1

HCID 24788029Ethyl 4-amino-1-benzylpiperidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Amino-1-benzyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester BH3 salt was heated in ethanol with NaOH 25%. After 72 h at 50° C. the mixture was cooled, washed with water/ice and extracted with AcOEt. The extract was washed with brine and dried over sodium sulfate. Removal of the solvent under reduced pressure gave an yellow oil. To a suspension of 4-amino-1-benzyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester (21 g) in 200 ml THF was added 50 ml TFA at 10° C. under an argon atmosphere. After stirring for 15 min at 0° C., NaBH4 (6.43 g) was added over a period of 75 min at 10° C. The mixture was stirred for additional 90 min at 0° C. After adding 100 ml NH4Cl saturated, the solution was extracted two times with CH2Cl2. The combined extracts were washed with water/ice and brine and dried over sodium sulfate. Evaporation of the solvent gave a yellow oil of the title compound which was taken for the next step without purification

Workup

  1. washwashed with water/ice
  2. extractionextracted with AcOEt
  3. washThe extract was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent under reduced pressure
  6. customgave an yellow oil
  7. stirringThe mixture was stirred for additional 90 min at 0° C
  8. extractionthe solution was extracted two times with CH2Cl2
  9. washThe combined extracts were washed with water/ice and brine
  10. dry with materialdried over sodium sulfate
  11. customEvaporation of the solvent

Sources & evidence

ORD record
ord-bbb081a7f64643799cfa87f676836767
Source dataset
uspto-grants-2010_03
Patent number
US07683079B2

Reaction notes

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