1,4-Bis(dihydroquinidine)phthalazine → (R)-1-(4-chloro-3-fluorophenyl)ethane-1,2-diol
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6]C(C=C)=[CH:4][C:3]=1[F:10].CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:32]C)C=C4)N(CC2)C1.[CH3:69][C:70]([OH:73])(C)[CH3:71].O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:69]([C@@H:70]([OH:73])[CH2:71][OH:32])=[CH:4][C:3]=1[F:10]Participants
4
Procedure
1-Chloro-2-fluoro-4-vinylbenzene (12.1 g, 77.3 mmol) was added to a cold (0° C.) solution of AD-mix-β (108 g, 139 mmol) in t-BuOH/H2O (600 mL; 1:1), and the mixture was allowed to warm up to room temperature overnight. The next day, the reaction was placed in an ice bath and quenched with solid Na2SO3 (114 g). The mixture was stirred for 1 hour and then extracted with ethyl acetate (3×500 mL). The combined organics were dried, filtered and concentrated to give (R)-1-(4-chloro-3-fluorophenyl)ethane-1,2-diol as an oil. The crude product was used in Step C without purification.
Workup
- customThe next day, the reaction was placed in an ice bath
- customquenched with solid Na2SO3 (114 g)
- extractionextracted with ethyl acetate (3×500 mL)
- customThe combined organics were dried
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5a5eee1250a247459ac6d24ce5fd2866
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09259470B2
Reaction notes
Loading…