Acetic Acid → HCID 58504078, Verbindung

HRID 2407828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2407828
[O:1]([C:8]1[C:13]2[C:14]([NH2:17])=[N:15][NH:16][C:12]=2[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18]([CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C1(C)C=CC=CC=1>[O:1]([C:8]1[C:13]2[C:14]([NH:17][CH2:18][CH:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH2:22][CH2:21]3)=[N:15][NH:16][C:12]=2[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 11615525HCID 11615525, Verbindung

Produkt 1

HCID 58504078HCID 58504078, VerbindungAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a stirred solution of the compound prepared in Example 434 (0.217 g,) in toluene (12 mL) was added tert-butyl 4-formylpiperidine-1-carboxylate (0.205 g). The mixture was evaporated in vacuo to remove water from imine formed. Sodium triacetoxyborohydride (0.244 g) was added, followed by acetic acid (0.4 mL). After stirring at room temperature for 1 hour, the reaction mixture was quenched with methanol slowly, to decompose excess borohydride, and then concentrated in vacuo. Ethyl acetate, was added to the residue and then washed with aqueous saturated sodium bicarbonate, dried, evaporated in vacuo to provide the title compound (0.262 g) with the following physical data.

Aufarbeitung

  1. customThe mixture was evaporated in vacuo
  2. customto remove water from imine
  3. customformed
  4. customthe reaction mixture was quenched with methanol slowly
  5. concentrationconcentrated in vacuo
  6. additionEthyl acetate, was added to the residue
  7. washwashed with aqueous saturated sodium bicarbonate
  8. customdried
  9. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-196501bd233b48269a043ef82c051583
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809538B2

Notizen zur Reaktion

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