Sodium Hydroxide → HCID 53996703, compound

HRID 1655717Notes

Reaction equation

HRID 1655717 reaction equation
C(C(C(=O)C1CNCCO1)C(O)=O)C1C=CC=CC=1.[CH3:20][O:21][C:22](=[O:34])[CH:23]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:24]([OH:26])=O.C([O:37][C:38]([CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)=[O:39])C.[OH-].[Na+]>CO.O>[CH3:20][O:21][C:22]([CH:23]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:24]([N:43]1[CH2:44][CH2:45][CH:40]([C:38]([OH:39])=[O:37])[CH2:41][CH2:42]1)=[O:26])=[O:34]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 70770Ethyl 4-piperidinecarboxylateHCID 10921701HCID 10921701, compoundHCID 19790783HCID 19790783, compound

Product 1

HCID 53996703HCID 53996703, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In a manner analogous to that described for the preparation of α-benzyltetrahydro-β-oxo-4H-1,4-oxazinepropionic acid, benzylmalonic acid monomethyl ester was amidated with piperidine-4-carboxylic acid ethyl ester and the resulting compound [MS: 347 (M)+ ]was saponified with 1N sodium hydroxide solution in a mixture of methanol and water at 0° for 2 hours. The crude product obtained was purified by chromatography on silica gel with a 95:5:2 mixture of chloroform, ethanol and ethyl acetate and recrystallized from a mixture of methanol, methylene chloride and ether, to yield 1-[α-(methoxycarbonyl)hydrocinnamoyl]-4-piperidinecarboxylic acid, melting point 138°.

Workup

  1. customThe crude product obtained
  2. customwas purified by chromatography on silica gel with a 95:5:2 mixture of chloroform, ethanol and ethyl acetate
  3. customrecrystallized from a mixture of methanol, methylene chloride and ether

Sources & evidence

ORD record
ord-56c632f351694c1aa18f54a2b8fd5d35
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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