1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-Butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate

HRID 456733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456733
[C:1]([O:5][C:6]([N:8]1[C@H:13]([C:14]([OH:16])=O)[C@H:12]2[CH2:17][C@@H:9]1[C@H:10]([OH:18])[CH2:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[C:25]#[N:26].CN(C)CCCN=C=NCC>CN(C)C=O>[C:25]([C@@H:21]1[CH2:22][CH2:23][CH2:24][N:20]1[C:14]([C@@H:13]1[C@H:12]2[CH2:17][C@H:9]([C@H:10]([OH:18])[CH2:11]2)[N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:16])#[N:26]

Komponenten

5

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 44593801(2S)-Pyrrolidine-2-carbonitrile hydrochlorideHCID 69133789(1R,3S,4S,6R)-2-(tert-Butoxycarbonyl)-6-hydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylic Acid

Produkt 1

HCID 86598896tert-Butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylateAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (1R,3S,4S,6R)-2-(tert-butoxycarbonyl)-6-hydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylic acid obtained in Example 5-6 (90 mg) in N,N-dimethylformamide (1.6 mL), was added (2S)-2-pyrrolidinecarbonitrile hydrochloride (55.7 mg) 1-hydroxy-7-azabenzotriazole (57.2 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (65 mg). The mixture was then stirred at room temperature for 6 hrs. The resulting mixture was evaporated in vacuo and the residue was chromatographed on silica gel eluting with ethyl acetate to give the target compound (85.4 mg) as a solid.

Aufarbeitung

  1. customThe resulting mixture was evaporated in vacuo
  2. customthe residue was chromatographed on silica gel eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c7dbfd21f5a14ebf8d88e09cb31af385
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186731B2

Notizen zur Reaktion

Wird geladen…