Pyridine → HCID 86707398, Verbindung

HRID 338827

Reaktionsgleichung

Reaktionsgleichung von HRID 338827
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@:13]([CH3:19])([C:16](O)=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.[N:35]1C=CC=CC=1.[NH4+].[OH-].O>C(OCC)(=O)C.O>[C:16]([C@@:13]1([CH3:19])[CH2:14][CH2:15][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:12]1)(=[O:17])[NH2:35]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 90495Di-tert-butyl dicarbonateHCID 76853756HCID 76853756, VerbindungHCID 86589665Water ammonium hydroxide

Produkt 1

HCID 86707398HCID 86707398, VerbindungAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of (S)-1-(benzyloxycarbonyl)-3-methylpyrrolidine-3-carboxylic acid (32.87 g, 124.8 mmol), Boc2O (29.97 g, 137.3 mmol) in ethyl acetate (200 mL) was added pyridine (12.62 mL, 156.1 mmol) and the reaction mixture was stirred at ambient temperature for 3 hours. A solution of 28-30% w/w NH4OH/water (21.79 mL, 162.3 mmol) was added. The reaction was stirred at ambient temperature for 5 hours. Water (50 mL) was added. The organic layer was separated, washed with 1N HCl (50 mL) and brine, dried and concentrated under reduced pressure to give (S)-benzyl 3-carbamoyl-3-methylpyrrolidine-1-carboxylate (31.30 g, 119.3 mmol, 95.6% yield) as an oil.

Aufarbeitung

  1. stirringThe reaction was stirred at ambient temperature for 5 hours
  2. customThe organic layer was separated
  3. washwashed with 1N HCl (50 mL) and brine
  4. customdried
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a151995ce2644fc89a3d897ae133fc4c
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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