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tert-butyl [(3R,4S,5S)-4-hydroxy-4,5-dimethyl-1-(5-nitro-2,3-dihydrofuro[2,3-b]pyridin-4-yl)piperidin-3-yl]carbamate → tert-Butyl [(3R,4S,5S)-1-(5-amino-2,3-dihydrofuro[2,3-b]pyridin-4-yl)-4-hydroxy-4,5-dimethylpiperidin-3-yl]carbamate

HRID 1499630
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1499630
[OH:1][C@@:2]1([CH3:29])[C@@H:7]([CH3:8])[CH2:6][N:5]([C:9]2[C:14]([N+:15]([O-])=O)=[CH:13][N:12]=[C:11]3[O:18][CH2:19][CH2:20][C:10]=23)[CH2:4][C@H:3]1[NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25]>CO.[Pd]>[NH2:15][C:14]1[C:9]([N:5]2[CH2:6][C@H:7]([CH3:8])[C@@:2]([OH:1])([CH3:29])[C@H:3]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:4]2)=[C:10]2[CH2:20][CH2:19][O:18][C:11]2=[N:12][CH:13]=1
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Komponenten

4

Edukt 1

HCID 86726849tert-butyl [(3R,4S,5S)-4-hydroxy-4,5-dimethyl-1-(5-nitro-2,3-dihydrofuro[2,3-b]pyridin-4-yl)piperidin-3-yl]carbamate

Produkt 1

HCID 86726848tert-Butyl [(3R,4S,5S)-1-(5-amino-2,3-dihydrofuro[2,3-b]pyridin-4-yl)-4-hydroxy-4,5-dimethylpiperidin-3-yl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of tert-butyl [(3R,4S,5S)-4-hydroxy-4,5-dimethyl-1-(5-nitro-2,3-dihydrofuro[2,3-b]pyridin-4-yl)piperidin-3-yl]carbamate (68 mg, 0.17 mmol) in MeOH (3.0 mL), 10 wt % Pd on carbon (25 mg) was added. The reaction mixture was stirred at room temperature under a hydrogen atmosphere (balloon pressure) for 6 h. The mixture was filtered through a pad of diatomaceous earth (eluted with MeOH), and then concentrated under reduced pressure. The resulting crude product was used directly in the next step without further purification (62 mg, 98%). LCMS calc. for C19H31N4O4 (M+H)+: m/z=379.2. found 379.0.

Aufarbeitung

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth (eluted with MeOH)
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting crude product was used directly in the next step without further purification (62 mg, 98%)

Quellen und Nachweise

ORD-Eintrag
ord-41e7000374104d2ba4cd99a3eac96408
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09200004B2

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