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Methanol → cis(+/-)-Benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamate

HRID 43601
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 43601
Cl.C(OCC)(=O)C.[CH2:8]([O:15][C:16]([NH:18][C@H:19]1[CH2:24][CH2:23][N:22]([C:25](OC(C)(C)C)=[O:26])[CH2:21][C@H:20]1[O:32][CH3:33])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C[Si]([N:38]=C=O)(C)C.CO>C(OCC)(=O)C>[C:25]([N:22]1[CH2:23][CH2:24][C@H:19]([NH:18][C:16](=[O:17])[O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@H:20]([O:32][CH3:33])[CH2:21]1)(=[O:26])[NH2:38]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 70696Trimethylsilyl isocyanateHCID 21866389Hydrogen chloride-ethyl acetateHCID 86648489tert-Butyl cis(+/-)-4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidine-1-carboxylate

Produkt 1

HCID 131730860cis(+/-)-Benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 4 N hydrochloric acid/ethyl acetate solution (30 ml, 120 mmol) was added to a solution of tert-butyl cis(±)-4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidine-1-carboxylate obtained in Example (103a) in ethyl acetate (10 mL). The mixture was stirred for 45 minutes and the solvent was evaporated under reduced pressure. The residue was diluted with dichloromethane, washed with a 1 N aqueous sodium hydroxide solution and brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. Trimethylsilyl isocyanate (0.86 g, 7.5 mmol) was added to the resulting residue, and the mixture was stirred at room temperature for 15 hours. Methanol (1 mL) was added, followed by stirring for 30 minutes. The precipitated solid was filtered off and washed with dichloromethane to obtain 1.44 g of the title compound as a colorless solid (81%).

Aufarbeitung

  1. customthe solvent was evaporated under reduced pressure
  2. additionThe residue was diluted with dichloromethane
  3. washwashed with a 1 N aqueous sodium hydroxide solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. stirringthe mixture was stirred at room temperature for 15 hours
  7. stirringby stirring for 30 minutes
  8. filtrationThe precipitated solid was filtered off
  9. washwashed with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-cdd9ad254116463698dae8d73b8a1ec2
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08536197B2

Notizen zur Reaktion

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