反应 #674319

反应方程式

compound

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

phenol

triphenylphosphine

diisopropyl azodicarboxylate

→

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

溶剂

DCM

toluene

ether

反应条件

后处理

1. 1
   萃取the solution was extracted with aqueous 3N NaOH
2. 2
   洗涤The organic layer was washed with brine
3. 3
   干燥dried over MgSO4
4. 4
   浓缩concentrated in vacuo

实验过程

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%).

来源