Boron trifluoride etherate → 4-Allyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

온도

0 °C

To a stirred solution of 4-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (1 g, 4.11 mmol) in THF (10 mL), tetraallyltin (1.08 mL, 4.52 mmol) in dry THF was added, then cooled to 0° C. before borontrifluoride etherate (0.520 mL, 4.11 mmol) was added drop wise. The mixture was stirred at 0° C. for 1 h and then at room temperature for an additional 2 hours. Potassium fluoride (360 mg in 5 mL water) and celite (1 g) was added and the reaction mixture was stirred for an hour. The reaction mixture was filtered and concentrated to dryness and the residue was dissolved in DCM (200 mL), washed with water (100 mL) and brine 100 mL), dried over MgSO4 and evaporated to dryness. The residue obtained on removal of solvent was purified by silica gel column chromatography using 50% EtOAc in hexanes to obtain 4-allyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (0.94 g, 80%).

1. additionwas added drop wise
2. waitat room temperature for an additional 2 hours
3. stirringthe reaction mixture was stirred for an hour
4. filtrationThe reaction mixture was filtered
5. concentrationconcentrated to dryness
6. dissolutionthe residue was dissolved in DCM (200 mL)
7. washwashed with water (100 mL) and brine 100 mL),
8. dry with materialdried over MgSO4
9. customevaporated to dryness
10. customThe residue obtained on removal of solvent
11. customwas purified by silica gel column chromatography

ORD 기록

ord-39c4b4eea1d54831902c5a469f1a4e71

출처 데이터셋

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07199105B2