Acetone → Benzyl 3,4-dihydroxypyrrolidine-1-carboxylate

To a solution of N-carbobenzoxy-3-pyrroline (1.00 g, 4.92 mmol, 1.0 eq) in acetone (20 mL) was added NMO (1.0 g, 7.38 mmol, 1.5 eq) followed by OsO4 (cat. 10 mg in 1 mL iPrOH). The mixture was stirred for 3 h. To this, saturated NaHSO3 aqueous solution (5 mL) was added, and the mixture was stirred for another 0.5 h. The organic phase was separated from the mixture, and the water phase was extracted with EtOAc (20 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (EtOAc) to give the compound as colorless oil (1.16 g, 100%).

1. stirringthe mixture was stirred for another 0.5 h
2. customThe organic phase was separated from the mixture
3. extractionthe water phase was extracted with EtOAc (20 mL×3)
4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationThe filtrate was concentrated in vacuo
7. customthe residue was purified by a silica gel column chromatography (EtOAc)

ORD 기록

ord-d494025b343d4d24af84fb2c3a7cbd17

출처 데이터셋

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09181277B2