Sodium Bicarbonate → (S)-Benzyl piperidine-2-carboxylate

HRID 54497

Reaction equation

HRID 54497 reaction equation
[NH:1]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:2]1[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH:1]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:2]1[C:3]([O:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:4]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 12436232Benzyl piperidine-2-carboxylate

Product 1

HCID 12436231(S)-Benzyl piperidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Benzyl pipecolate was routinely generated by treating an ethyl acetate suspension of this salt with saturated sodium bicarbonate until dissolution of the organic material. The aqueous layer was extracted twice with ethyl acetate and the combined organic extracts were dried with MgSO4 and evaporated to yield (S)-Benzyl pipecolate (15) as a pale yellow oil.

Workup

  1. additionby treating
  2. dissolutionuntil dissolution of the organic material
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. dry with materialthe combined organic extracts were dried with MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-f218f10babd54387b3ff407e2cd3e023
Source dataset
uspto-grants-1997_04
Patent number
US05622970

Linked notes

Loading…