Methyl(3S,4R)-1-benzyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylate → methyl (3S,4R)-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylate

HRID 1992666Notes

Reaction equation

C([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[F:20])[C@H:10]([C:21]([O:23][CH3:24])=[O:22])[CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[F:20][C:14]1[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]=1[C@@H:11]1[CH2:12][NH:8][CH2:9][C@H:10]1[C:21]([O:23][CH3:24])=[O:22]

Participants

Conditions

Temperature: 40 °C

Procedure

To a suspension of methyl (3S,4R)-1-benzyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylate, from preparation 20 (15 g, 45 mmol) in ethanol (225 mL) at room temperature under dry nitrogen was added 10% palladium on carbon (Degussa type) (1.5 g), and the reaction mixture placed under 50 psi pressure of hydrogen, and heated to 40° C. overnight. After cooling to room temperature, the reaction mixture was filtered through Celite® and concentrated in vacuo to afford the title compound as an orange oil (10.8 g, 98%).

Workup

temperatureAfter cooling to room temperature
filtrationthe reaction mixture was filtered through Celite®
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-13d0409745af43b9a66f1fd660c4a5e4
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07649002B2

Reaction notes

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