Sodium Carbonate → HCID 58200306, compound

To a stirred room temperature suspension of P4S10 (6.0 g, 13.4 mmol) and Na2CO3 (1.42 g, 13.4 mmol) in THF (40 mL) was slowly added a solution of (R)-5-(3-fluoro-phenyl)-morpholin-3-one (2.16 g, 11.1 mmol) in THF (30 mL). The mixture was stirred at room temperature for two hours, and then quenched by addition of 10% aqueous Na3PO4 (50 mL). The mixture was stirred another five minutes and then extracted with a 1:1: mixture of ethyl acetate and diethyl ether. The organic layer was separated, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was chromatographed through silica gel using a 15-30% ethyl acetate/hexanes solvent gradient to give 1.84 g (78%) of (R)-5-(3-fluoro-phenyl)-morpholine-3-thione as a white solid, MP=124-125° C.

1. customquenched by addition of 10% aqueous Na3PO4 (50 mL)
2. stirringThe mixture was stirred another five minutes
3. extractionextracted with a 1:1
4. additionmixture of ethyl acetate and diethyl ether
5. customThe organic layer was separated
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe residue was chromatographed through silica gel using a 15-30% ethyl acetate/hexanes solvent gradient

ORD record

ord-2309932ffda7495ab6ee7e5d0078197b

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871760B2