1,3-Dihydro-5-nitro-1'-((2-(trimethylsilyl)ethoxy)methyl)spiro(2H-indene-2,3'-(3H)pyrrolo(2,3-b)pyridin)-2'(1'H)-one → (S)-5-Amino-1'-((2-(trimethylsilyl)ethoxy)methyl)-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'h)-one

HRID 550971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 550971
[N+:1]([C:4]1[CH:5]=[C:6]2[C:27](=[CH:28][CH:29]=1)[CH2:26][C:8]1([C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:9]1=[O:25])[CH2:7]2)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:27](=[CH:28][CH:29]=1)[CH2:26][C@@:8]1([C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:22])([CH3:23])[CH3:24])[C:9]1=[O:25])[CH2:7]2

Komponenten

4

Edukt 1

HCID 591667381,3-Dihydro-5-nitro-1'-((2-(trimethylsilyl)ethoxy)methyl)spiro(2H-indene-2,3'-(3H)pyrrolo(2,3-b)pyridin)-2'(1'H)-one

Produkt 1

HCID 67016448(S)-5-Amino-1'-((2-(trimethylsilyl)ethoxy)methyl)-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'h)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 10% Pd/C (3 g) and (±)-5-nitro-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1H)-one from Step A (19.1 g, 46.4 mmol) was stirred vigorously in EtOH (400 mL) under an atmosphere of hydrogen (ca. 1 atm). After 18 h, the mixture was filtered through a pad of Celite, washing extensively with MeOH, and the filtrate was concentrated in vacuo to give the crude racemic compound. The enantiomers were resolved by HPLC, utilizing a Chiralcel OD column and eluting with MeOH. The first major peak to elute was (S)-5-amino-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one, the title compound, and the second major peak to elute was (R)-5-amino-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one. MS: m/z=382 (M+1).

Aufarbeitung

  1. filtrationthe mixture was filtered through a pad of Celite
  2. washwashing extensively with MeOH
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give the crude racemic compound
  5. washeluting with MeOH
  6. washThe first major peak to elute
  7. washthe title compound, and the second major peak to elute

Quellen und Nachweise

ORD-Eintrag
ord-c03ec81cc9604534b31762ee8bf97573
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947677B2

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