Reaktion #969947

Reaktionsgleichung

(1R,4R)-5-acetyl-2-oxa-5-aza-bicyclo[2.2.1]heptan-3-one

[1,4]diazepane

→

title compound

Ausbeute 72.0%

(2R,4R)-1-[2-([1,4]Diazepane-1-carbonyl)-4-hydroxy-pyrrolidin-1-yl]-ethanone

Ausbeute 72.0%

Lösungsmittel

t-amyl alcohol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture was then concentrated
2. 2
   Sonstigeto remove t-amyl alcohol (2.4 L)
3. 3
   FiltrationThe resulting slurry was filtered
4. 4
   Waschenwashed with EtOAc (1 L)

Vorschrift

A mixture of (1R,4R)-5-acetyl-2-oxa-5-aza-bicyclo[2.2.1]heptan-3-one (310.3 g, 2.0 mol) and [1,4]diazepane (500.85 g, 5 mol) in t-amyl alcohol (3.0 L) was held at 90° C. for 17 h. The mixture was then concentrated to remove t-amyl alcohol (2.4 L). The resulting slurry was filtered and washed with EtOAc (1 L) to provide the title compound as a solid (367 g, 72%). MS (ESI): mass calcd. for C12H21N3O3, 255.2; m/z found, 256.2 [M+H]+. 1H NMR (CDCl3): 5.95 (br s, 1H), 4.93-4.68 (m, 1H), 4.48-4.32 (m, 1H), 3.90-3.65 (m, 5H), 3.54-3.41 (m, 1H), 3.12-2.74 (m, 4H), 2.32-2.22 (m, 1H), 2.16-1.68 (m, 6H).

Quelle