Methanol → lithium 1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

HRID 627015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627015
[N:1]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3][CH:2]1[C:10]([O:12]CC)=[O:11].CO.[Li+:24].[OH-]>C1COCC1>[C:18]([O:17][C:15]([N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3][CH:2]1[C:10]([O-:12])=[O:11])=[O:16])([CH3:21])([CH3:19])[CH3:20].[Li+:24]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 691087141-tert-butyl 2-ethyl 2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1,2-dicarboxylate

Produkt 1

HCID 118380491lithium 1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-tert-butyl 2-ethyl 2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1,2-dicarboxylate (prepared using methods of M Boehringer, et al. U.S. Pat. No. 7,417,144) (200 mg, 684 μmol, Eq: 1.00) in THF (1.2 mL) and MeOH (0.8 mL) was added LiOH (16.4 mg, 684 μmol, Eq: 1.00) in one portion. The reaction mixture was stirred at rt for 72 h. The reaction mixture was concentrated in vacuo and the residue treated with DCM (10 mL) to give lithium 1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate as an off-white solid (200 mg) which was used without further purification.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue treated with DCM (10 mL)

Quellen und Nachweise

ORD-Eintrag
ord-a1212a436ae746ca8ee1a93a798deef3
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309248B2

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