(4aS-cis-)-6-benzyl-octahydropyrrolo(3.4-b)pyridine → (4aS,7aS)-tert-butyl 6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate

HRID 2356382

Reaktionsgleichung

Reaktionsgleichung von HRID 2356382
[CH2:1]([N:8]1[CH2:16][C@@H:15]2[C@@H:10]([CH2:11][CH2:12][CH2:13][NH:14]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC([O-])=O)([O:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=O)=O>CO>[CH2:1]([N:8]1[CH2:16][C@@H:15]2[C@@H:10]([CH2:11][CH2:12][CH2:13][N:14]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 10198297(4aS-cis-)-6-benzyl-octahydropyrrolo(3.4-b)pyridineHCID 86600350tert-Butoxycarbonyl dicarbonate

Produkt 1

HCID 29973012(4aS,7aS)-tert-butyl 6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylateAusbeute 97,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The preparation comprises stirring [1S,6S]-8-benzyl-2,8-diazabicyclo[4,3,0]nonane (5.0 g, 23.1 mmol) in methanol (50 mL) at room temperature, adding batchwise tertbutyloxycarbonyl dicarbonate (5.1 g, 23.4 mmol), stirring for 0.5 h, vacuum distilling to remove solvent, and column chromatographing with petroleum ether and ethyl, acetate at the ratio of 10:1 to give [1S,6S]-8-benzyl-2-tertbutyloxycarbonyl-2,8-diazabicyclo[4,3,0]nonane (7.1 g, 97.2%), [α]20D=−72.4° (CHCl3, C=5).

Aufarbeitung

  1. distillationvacuum distilling
  2. customto remove solvent, and column chromatographing with petroleum ether and ethyl, acetate at the ratio of 10:1

Quellen und Nachweise

ORD-Eintrag
ord-c5f83b656f624b4bb5c4bcbce28be9d5
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759362B2

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