tert-Butyl 3-(aminomethyl)pyrrolidine-1-carboxylate → HCID 67225102, Verbindung

HRID 1968185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1968185
[CH:1]([C:3]1[C:11]2[C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=[N:7][C:6]=2[N:5]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:4]=1)=O.[NH2:23][CH2:24][CH:25]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26]1.C([BH3-])#N.[Na+]>CO.CC(O)=O>[C:33]([O:32][C:30]([N:27]1[CH2:28][CH2:29][CH:25]([CH2:24][NH:23][CH2:1][C:3]2[C:11]3[C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=[N:7][C:6]=3[N:5]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:4]=2)[CH2:26]1)=[O:31])([CH3:36])([CH3:35])[CH3:34]

Komponenten

6

Edukt 3

HCID 2756485tert-Butyl 3-(aminomethyl)pyrrolidine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 582935211-tert-Butyl 4-methyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate

Produkt 1

HCID 67225102HCID 67225102, VerbindungAusbeute 85,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1-tert-butyl 4-methyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate (91 mg, 0.3 mmol) in MeOH (2 mL) was added AcOH (5 drops) and tert-butyl 3-(aminomethyl)pyrrolidine-1-carboxylate (90 mg, 0.45 mmol). After stirring for 60 min at rt, the reaction mixture was cooled to 0° C. Sodium cyanoborohydride (57 mg, 0.9 mmol) was added, and the reaction mixture was stirred for an additional 3 h at rt. The mixture was quenched with water and extracted with ethyl acetate. The combined organic layers washed with saturated NaHCO3 and with brine, dried over Na2SO4, and concentrated in vacuo to give 125 mg of crude 1-tert-butyl 4-methyl 3-(((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate as a colorless oil which was used without further purification. [M+H] found 489.40.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to 0° C
  2. stirringthe reaction mixture was stirred for an additional 3 h at rt
  3. customThe mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers washed with saturated NaHCO3 and with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7ea7d19a6d74425eaf0c4b9254ca8e7f
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420816B2

Notizen zur Reaktion

Wird geladen…