4-Fluorobenzaldehyde → HCID 68715731, compound

Temperature

-40 °C

To a stirred, cooled (−78° C.) solution of (S)-4-(benzothiazole-2-sulfonylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.484 mg) in THF (12 ml) under an argon atmosphere was added slowly a 1 M solution of LiHMDS in THF (1.1 ml). The mixture was warmed to −40° C. and stirring at that temperature was continued for 30 min. The mixture was cooled again to −78° C. and a solution of 4-fluorobenzaldehyde (0.112 g) in THF (3 ml) was then added slowly via a syringe. Stirring at −78° C. was continued for 2 h, and then the reaction mixture was slowly allowed to warm to 0° C. The mixture was quenched by the addition of sat. aq. NH4Cl (15 ml) and H2O (15 ml) and extracted with EtOAc. The aqueous phase was back extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (SiO2; gradient: cyclohexane ->cyclohexane/EtOAc 85:15) to give (R)-4-[(E)-2-(4-fluoro-phenyl)-vinyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.201 g) as colorless viscous oil. MS (ISP): 322.4 ([M+H]+))

1. temperatureThe mixture was cooled again to −78° C.
2. stirringStirring at −78° C.
3. waitwas continued for 2 h
4. temperatureto warm to 0° C
5. customThe mixture was quenched by the addition of sat. aq. NH4Cl (15 ml) and H2O (15 ml)
6. extractionextracted with EtOAc
7. extractionThe aqueous phase was back extracted with EtOAc
8. washThe combined organics were washed with brine
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated
12. customThe crude product was purified by column chromatography (SiO2; gradient: cyclohexane ->cyclohexane/EtOAc 85:15)

ORD record

ord-109cd1b324d44fe09b66eade615061a9

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604061B2