Lithium Hydroxide → HCID 16202336, compound
Reaction equation
[OH-].[Li+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C@@H:11]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][C@H:12]1[C:23]([O:25]C)=[O:24]>O1CCCC1>[C:19]([O:18][C:16]([N:14]1[CH2:15][C@@H:11]([C:5]2[CH:6]=[CH:7][C:8]([F:10])=[CH:9][C:4]=2[F:3])[C@H:12]([C:23]([OH:25])=[O:24])[CH2:13]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Lithium hydroxide (130 mg, 23.5 mmol) was added dropwise to a stirred solution of 1-tert-butyl 3-methyl (3S,4R)-4-(2,4-difluorophenyl)pyrrolidine-1,3-dicarboxylate, from preparation 52 (930 mg, 2.72 mmol) in tetrahydrofuran (10 mL) at room temperature. The reaction mixture was stirred for 48 hours, concentrated in vacuo and diluted with water (15 mL). The phases were separated and the aqueous phase was extracted with ethyl acetate (1×25 mL). The aqueous layer was acidified with 2M hydrochloric acid solution (2.7 mL) and further extracted with ethyl acetate (2×40 mL). The combined organic extracts were dried over magnesium sulfate, filtered, concentrated in vacuo and azeotroped with dichloromethane to give the desired product, 775 mg (87%).
Workup
- concentrationconcentrated in vacuo
- additiondiluted with water (15 mL)
- customThe phases were separated
- extractionthe aqueous phase was extracted with ethyl acetate (1×25 mL)
- extractionfurther extracted with ethyl acetate (2×40 mL)
- dry with materialThe combined organic extracts were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customazeotroped with dichloromethane
Sources & evidence
- ORD record
- ord-94fa2335daa047fca6fc92913e06c26e
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07649002B2
Reaction notes
Loading…