Potassium Hydroxide → 1-(Tert-butoxycarbonyl)-4,4-difluoro-2-[4-(5-fluoropyridin-2-yl)benzyl]proline

HRID 1881496Notes

Reaction equation

HRID 1881496 reaction equation
[OH-].[K+].[F:3][C:4]1([F:34])[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:6]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][N:28]=3)=[CH:23][CH:22]=2)([C:16]([O:18]C)=[O:17])[CH2:5]1>CS(C)=O.O>[C:12]([O:11][C:9]([N:7]1[CH2:8][C:4]([F:3])([F:34])[CH2:5][C@@:6]1([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][N:28]=2)=[CH:23][CH:22]=1)[C:16]([OH:18])=[O:17])=[O:10])([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 667056021-Tert-butyl 2-methyl 4,4-difluoro-2-[4-(5-fluoropyridin-2-yl)benzyl]pyrrolidine-1,2-dicarboxylate

Product 1

HCID 667056251-(Tert-butoxycarbonyl)-4,4-difluoro-2-[4-(5-fluoropyridin-2-yl)benzyl]proline

Reagents, catalysts & solvents 1

HCID 23503278(Methanesulfinyl)methane--water (1/1)Solvent

Procedure

Potassium hydroxide (61 mg, 1.1 mmol) was added to an ambient temperature solution of 1-tert-butyl 2-methyl 4,4-difluoro-2-[4-(5-fluoropyridin-2-yl)benzyl]pyrrolidine-1,2-dicarboxylate (246 mg, 0.55 mmol) in DMSO/water (1:1) (2 mL). After stirring at ambient temperature for 1 h, the reaction mixture was extracted with chloroform and concentrated in vacuo to afford 1-(tert-butoxycarbonyl)-4,4-difluoro-2-[4-(5-fluoropyridin-2-yl)benzyl]proline.

Workup

  1. extractionthe reaction mixture was extracted with chloroform
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ae96032bf884739849f2551dfff969e
Source dataset
uspto-grants-2012_11
Patent number
US08318767B2

Reaction notes

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