Pyridine → rac-(2'S,3'R,4'S,5'R)-2'-(3-acetoxy-2,2-dimethyl-propyl)-6-chloro-4'-(3-chloro-2-fluoro-phenyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid tert-butyl ester

To a solution of rac-(2′S,3′R,4′S,5′R)-6-chloro-4′-(3-chloro-2-fluoro-phenyl)-2′-(3-hydroxy-2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-5′-carboxylic acid tert-butyl ester (0.3 g, 0.56 mmol) in tetrahydrofuran (2 mL) at 0° C. was added pyridine (44 mg, 0.56 mmol) and acetyl chloride (44 mg, 0.56 mmol). The mixture was stirred at room temperature for 1 h. The mixture was concentrated, and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with water, saturated aqueous CuSO4, brine, dried over MgSO4, and concentrated to give as rac-(2′S,3′R,4′S,5′R)-2′-(3-acetoxy-2,2-dimethyl-propyl)-6-chloro-4′-(3-chloro-2-fluoro-phenyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-5′-carboxylic acid tert-butyl ester as a yellow oil (0.24 g, 74%)

1. concentrationThe mixture was concentrated
2. customthe residue was partitioned between ethyl acetate and water
3. customThe organic layer was separated
4. washwashed with water, saturated aqueous CuSO4, brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated

ORD-Eintrag

ord-921632b6ee3243468daff0109ab430ba

Quelldatensatz

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08088815B2