Pipecolic Acid → 1-(3-Benzyloxybenzoyl)-2-piperidinecarboxylic acid

HRID 380127

Reaktionsgleichung

Reaktionsgleichung von HRID 380127
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(OCC(C)C)=O.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[C:32]([OH:34])=[O:33].C([O-])(O)=O.[Na+]>C1COCC1.O.C(N(CC)CC)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[C:32]([OH:34])=[O:33])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 849Pipecolic AcidHCID 62365Isobutyl chloroformateHCID 3092263-(Benzyloxy)benzoic acidHCID 516892Sodium Bicarbonate

Produkt 1

HCID 183674161-(3-Benzyloxybenzoyl)-2-piperidinecarboxylic acidAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Triethylamine (3.36 ml) was added to a stirred solution of 3-benzyloxybenzoic acid (5.0 g) and isobutyl chloroformate (3.13 ml) in THF (67 ml) under ice-cooling and the resulting mixture was stirred at the same temperature for 1 hour. A solution of 2-piperidinecarboxylic acid (4.14 g) and NaHCO3 (3.32 g) in water (40 ml) was added dropwise to the stirred mixture at the same temperature and the mixture was stirred at the same temperature for 2 hours and at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and 1N HCl. The organic layer was separated, washed with 1N HCl (twice) and brine, dried over MgSO4, and evaporated in vacuo. The residue was chromatographed over silica gel to afford 1-(3-benzyloxybenzoyl)-2-piperidinecarboxylic acid (2.01 g) as a amorphous powder.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 2 hours and at room temperature overnight
  3. customThe reaction mixture was partitioned between ethyl acetate and 1N HCl
  4. customThe organic layer was separated
  5. washwashed with 1N HCl (twice) and brine
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo
  8. customThe residue was chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-729624d027f746eeb3938f65f3d118de
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300344B1

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