Reaktion #674319

Reaktionsgleichung

compound

tert-butyl (R)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

phenol

triphenylphosphine

diisopropyl azodicarboxylate

→

tert-butyl (R)-2-(phenoxymethyl)pyrrolidine-1-carboxylate

Lösungsmittel

DCM

toluene

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe solution was extracted with aqueous 3N NaOH
2. 2
   WaschenThe organic layer was washed with brine
3. 3
   Trocknendried over MgSO4
4. 4
   Einengenconcentrated in vacuo

Vorschrift

To an ice-cold solution of the compound from Step 1 (2.60 g, 12.9 mmol), phenol (3.64 g, 38.7 mmol), and triphenylphosphine (6.77 g, 25.8 mmol) in DCM (50 mL) was added a solution of diisopropyl azodicarboxylate (5.22 g, 25.8 mmol) in toluene (30 mL). After stirring at room temperature for 60 hours it was diluted with ether and the solution was extracted with aqueous 3N NaOH. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The intermediate tert-butyl (R)-2-(phenoxymethyl)pyrrolidine-1-carboxylate was obtained from the residue by column chromatography (silica gel, cHex/EtOAc 29:1); yield: 1.82 g (51%).

Quelle