Tributylphosphine → (S)-3-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)-1-phenylpyrrolidin-2-one

Prepared using general procedure 61: To a yellow solution of di-tert-butyl azo-dicarboxylate (2.23 g, 9.7 mmol) in THF (25 mL) at 0° C. under N2 was slowly added tributylphosphine (2.4 mL, 9.7 mmol), The resulting colorless solution of the Mitsunobu reagent was stirred at RT for 10 min, and then added to a solution of (S)-2-(6-Chloro-3,4-dihydroquinolin-1(2H)-yl)-4-hydroxy-N-phenylbutanamide (2.56 g, 7.4 mmol) in THF (25 mL) at 0° C. under N2. The reaction mixture was stirred for 10 min. at this temperature, and quenched by addition of a saturated aqueous NaHCO3 solution. EtOAc was added, the phases were separated, and the aqueous layer was extracted with EtOAc (2×). The combined organic extracts were dried over MgSO4 and concentrated. Purification via silica gel chromatography using 20-40 EtOAc in hexane gave (S)-3-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)-1-phenylpyrrolidin-2-one as a white solid (2.43 g, 100%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=327.5; tR=1.50 min.

1. customPrepared
2. customat 0° C.
3. customquenched by addition of a saturated aqueous NaHCO3 solution
4. additionEtOAc was added
5. customthe phases were separated
6. extractionthe aqueous layer was extracted with EtOAc (2×)
7. dry with materialThe combined organic extracts were dried over MgSO4
8. concentrationconcentrated
9. customPurification via silica gel chromatography

ORD 기록

ord-08ddca1249de4940b6647fa72ac1994f

출처 데이터셋

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08586589B2