Water → HCID 86628130, Verbindung

HRID 2354094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2354094
[NH:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.I[CH2:15][C:16]12[O:22][CH:19]([CH2:20][CH2:21]1)[CH2:18][CH2:17]2.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[C:16]12([CH2:15][N:1]3[CH2:5][CH2:4][C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:2]3)[O:22][CH:19]([CH2:20][CH2:21]1)[CH2:18][CH2:17]2

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 67035019HCID 67035019, Verbindung

Produkt 1

HCID 86628130HCID 86628130, VerbindungAusbeute 52,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

The mixture of tert-butyl (3R)-3-pyrrolidinylcarbamate (500 mg), 1-(iodomethyl)-7-oxabicyclo[2.2.1]heptane (639 mg) and K2CO3 (742 mg) in DMF (5 mL) was stirred at 75° C. for 32 hours. The resultant was added H2O, extracted with AcOEt. The organic phase was washed with brine, dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give tert-butyl [(3R)-1-(7-oxabicyclo[2.2.1]hept-1-ylmethyl)-3-pyrrolidinyl]carbamate (416 mg) as orange oil.

Aufarbeitung

  1. extractionextracted with AcOEt
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-22348c58282b464f8686b6ef8d6cd022
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07750155B2

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