Diisopropylethylamine → 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

HRID 1499629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1499629
I[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]2[O:11][CH2:12][CH2:13][C:3]=12.[OH:14][C@@:15]1([CH3:30])[C@@H:20]([CH3:21])[CH2:19][NH:18][CH2:17][C@H:16]1[NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].CCN(C(C)C)C(C)C>CCO>[OH:14][C@@:15]1([CH3:30])[C@@H:20]([CH3:21])[CH2:19][N:18]([C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]3[O:11][CH2:12][CH2:13][C:3]=23)[CH2:17][C@H:16]1[NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 867266754-Iodo-5-nitro-2,3-dihydrofuro[2,3-b]pyridineHCID 86726846tert-Butyl [(3R,4S,5S)-4-hydroxy-4,5-dimethylpiperidin-3-yl]carbamate

Produkt 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]carbamateAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a vial containing 4-iodo-5-nitro-2,3-dihydrofuro[2,3-b]pyridine (76 mg, 0.26 mmol) and tert-butyl [(3R,4S,5S)-4-hydroxy-4,5-dimethylpiperidin-3-yl]carbamate (60 mg, 0.24 mmol), EtOH was added (2.0 mL), followed by DIPEA (114 mg, 0.883 mmol). The mixture was stirred at 110° C. for 12 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The resulting residue was purified on silica gel (0-100% EtOAc in hexanes) to give the sub-title compound as a yellow foamy solid (68 mg, 69%). LCMS calc. for C19H29N4O6 (M+H)+: m/z=409.2. found 409.0.

Aufarbeitung

  1. additionwas added (2.0 mL)
  2. temperatureAfter cooling to room temperature
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe resulting residue was purified on silica gel (0-100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-06132a0dcf874ebd837a36817d3aa324
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09200004B2

Notizen zur Reaktion

Wird geladen…