Ammonia → (2S)-N-(tert-Butyloxycarbonyl)piperidine-2-carboxamide

HRID 1927802Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1927802
[C:1]([O:5][C:6](N1CCCC[C@H]1C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH2:17].O[N:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=N1.CCN=C=NCCCN(C)C.Cl.N>C(Cl)Cl.CN(C=O)C>[C:1]([O:5][C:6]([NH:19][C:23]([C@@H:24]1[CH2:25][CH2:26][CH2:27][CH2:22][NH:21]1)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 688617(2S)-1-((tert-butoxy)carbonyl)piperidine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 51534906(2S)-N-(tert-Butyloxycarbonyl)piperidine-2-carboxamideAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22350042dichloromethane N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

(2S)—N-(tert-Butyloxycarbonyl)pipecolinic acid (3.0 g, 13.0 mmol) was dissolved in CH2Cl2/DMF (9:1, 150 ml). To this solution at 0° C. was added 1-hydroxybenzotriazole hydrate (2.0 g, 14.8 mmol) and water soluble carbodiimide (2.74 g, 13.7 mmol). After 1 h at 0° C. ammonia (35%, 25 ml) was added. After 18 h at 0° C. to room temperature the solvent was removed in vacuo and the residue was taken up in ethyl acetate (500 ml). This solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (eluant: 4% methanol, 96% chloroform) to give a white solid identified as the title compound (1.7 g, 7.4 mmol, 57%).

Aufarbeitung

  1. customAfter 18 h at 0° C. to room temperature the solvent was removed in vacuo
  2. washThis solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (eluant: 4% methanol, 96% chloroform)
  6. customto give a white solid

Quellen und Nachweise

ORD-Eintrag
ord-1697183e0e4d4b59ba5c7d412c9ba43b
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183280B2

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