Ethanol → Nipecotic Acid

HRID 1786008Notes

Reaction equation

HRID 1786008 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8](C2C=CC(C(N3C4C(=CC=CC=4)[C@H](N(C(=O)C)C4C=CC(Cl)=CC=4)C[C@@H]3C)=O)=CC=2)[CH2:7]1)=[O:5])C.C(O)C.[OH-].[Li+]>O1CCCC1>[NH:8]1[CH2:9][CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7]1

Participants

5

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 57595450HCID 57595450, compound

Product 1

HCID 4498Nipecotic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

(2S,4R)-1-(4-{4-[Acetyl-4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-piperidine-3-carboxylic acid was prepared from (2S,4R)-1-(4-{4-[acetyl(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-piperidine-3-carboxylic acid ethyl ester (0.300 g, 0.522 mol) was hydrolyzed to the acid by dissolving in tetrahydrofuran and ethanol and lithium hydroxide (1N) was added and heated 50° C. for 2 h. The mixture was cooled to room temperature, acidified to form a white precipitate. The solid was filtered to give to afford the product after HPLC purification.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customto form a white precipitate
  3. filtrationThe solid was filtered
  4. customto give
  5. customto afford the product
  6. customafter HPLC purification

Sources & evidence

ORD record
ord-e550599a1e904c7c8d19a49f5e3d48ca
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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