7-(3-benzyloxy-benzenesulfonyl)-3,4-dihydro-1H-benzofuro[2,3-c]pyridine-2-carboxylic acid tert-butyl ester → 3-(1,2,3,4-Tetrahydro-benzo[4,5]furo[2,3-c]pyridine-7-sulfonyl)-phenol

HRID 1616894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616894
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[C:14]3[CH:20]=[CH:19][C:18]([S:21]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30]CC5C=CC=CC=5)[CH:25]=4)(=[O:23])=[O:22])=[CH:17][C:15]=3[O:16][C:10]=2[CH2:9]1)=O)(C)(C)C>CO.CCOC(C)=O.[Pd]>[CH2:9]1[C:10]2[O:16][C:15]3[CH:17]=[C:18]([S:21]([C:24]4[CH:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=4)(=[O:22])=[O:23])[CH:19]=[CH:20][C:14]=3[C:11]=2[CH2:12][CH2:13][NH:8]1

Komponenten

5

Edukt 1

HCID 673238427-(3-benzyloxy-benzenesulfonyl)-3,4-dihydro-1H-benzofuro[2,3-c]pyridine-2-carboxylic acid tert-butyl ester

Produkt 1

HCID 673256153-(1,2,3,4-Tetrahydro-benzo[4,5]furo[2,3-c]pyridine-7-sulfonyl)-phenol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 7-(3-benzyloxy-benzenesulfonyl)-3,4-dihydro-1H-benzofuro[2,3-c]pyridine-2-carboxylic acid tert-butyl ester (50 mg, 0.1 mmol) in 5 mL methanol and 1 mL EtOAc was added Pd black (10% on carbon, 45 mg, 3.4 mmol). The mixture was kept under hydrogenation at 40 psi overnight and the solvent was evaporated. After filtration, the debenzylated product was taken to the next step without further purification. Removal of N-Boc protecting group with 4N HCl using a general procedure afforded the title product. mp 279-281° C., MS m/z 330 [M+H]+. 1H-NMR (400 MHz, DMSOd6): δ 10.26 (s, 1H), 9.76 (br s, 2H), 8.24 (s, 1H), 7.84 (m, 2H), 7.39 (m, 2H), 7.30 (s, 1H), 7.02 (m, 1H), 4.47 (s, 2H), 3.44 (m, 2H), 2.94 (m, 2H).

Aufarbeitung

  1. customwas kept under hydrogenation at 40 psi overnight
  2. customthe solvent was evaporated
  3. filtrationAfter filtration
  4. customthe debenzylated product was taken to the next step without further purification
  5. customRemoval of N-Boc protecting group with 4N HCl using a general procedure

Quellen und Nachweise

ORD-Eintrag
ord-69dd6b55d4d649cf90285eb491d637a9
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765779B2

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