Lithium hydroxide, monohydrate → 3-Tert-butyl-4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

HRID 601796Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 601796
[C:1]([C:5]1[C:6]2[C:16](=[O:17])[CH2:15][CH2:14][C:7]=2[NH:8][C:9]=1[C:10]([O:12]C)=[O:11])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>>[C:1]([C:5]1[C:6]2[C:16](=[O:17])[CH2:15][CH2:14][C:7]=2[NH:8][C:9]=1[C:10]([OH:12])=[O:11])([CH3:4])([CH3:2])[CH3:3]

Komponenten

3

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 59180105HCID 59180105, Verbindung

Produkt 1

HCID 441249833-Tert-butyl-4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acidAusbeute 37,4 %

Versuchsvorschrift

The title compound was synthesized from methyl 3-tert-butyl-4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (33 mg, 0.14 mmol) and lithium hydroxide monohydrate (30 mg, 0.71 mmol) according to General Procedure 7. Purification by reverse phase semi-preparative HPLC provided a pure fraction (11.6 mg, 37%) of 3-tert-butyl-4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (3). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.46 (s, 9H), 2.82-2.90 (m, 4H); LCMS-MS (ESI+) 221.7 (M−H); HPLC (UV=95.8%).

Aufarbeitung

  1. customPurification by reverse phase semi-preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-bacdf85a64c1413884bcf3317911f879
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902252B2

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