Acetic Acid → HCID 69545831, Verbindung

HRID 2086254Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2086254
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)[C:10]1=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([NH:14][CH:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[CH2:19][CH2:20]2)[C:10]1=[O:27])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 69545990(3S)-3-(tert-butoxycarbonylamino)-1-[1-(4-pyridyl)-4-piperidinylideneamino]-2-pyrrolidone

Produkt 1

HCID 69545831HCID 69545831, VerbindungAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

(3S)-3-(tert-Butoxycarbonylamino)-1-[1-(4-pyridyl)-4-piperidinylideneamino]-2-pyrrolidone (3.57 g) was dissolved in methanol (40 ml), combined with acetic acid (2.05 g) with cooling on ice, followed by sodium cyanoborohydride (807 mg) and stirred at room temperature for 30 minutes. The reaction mixture was concentrated, and the residue was combined with an aqueous solution of sodium hydroxide, extracted with dichloromethane, dried, concentrated, and purified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1) to obtain the title compound (2.56 g) as a colorless amorphous material.

Aufarbeitung

  1. temperaturewith cooling on ice
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with dichloromethane
  4. customdried
  5. concentrationconcentrated
  6. custompurified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-813ac87904194d809ac3afa2643898db
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06723722B1

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