Sodium Hydroxide → (4S)-1-tert-Butoxycarbonyl-4-fluoro-L-proline

HRID 456736Notes

Reaction equation

HRID 456736 reaction equation
[F:1][C@@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16]C)=[O:15])[CH2:3]1.[OH-].[Na+]>CO>[C:10]([O:9][C:7]([N:5]1[CH2:6][C@@H:2]([F:1])[CH2:3][C@H:4]1[C:14]([OH:16])=[O:15])=[O:8])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 109777731,2-Pyrrolidinedicarboxylic acid, 4-fluoro-, 1-(1,1-dimethylethyl) 2-methyl ester, (2R,4R)-rel-

Product 1

HCID 2756017(4S)-1-tert-Butoxycarbonyl-4-fluoro-L-proline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude product of 1-tert-butyl 2-methyl (2S,4S)-4-fluoro-1,2-pyrrolidinedicarboxylate obtained in Example 7-6 (127.5 g) was dissolved in methanol (400 mL) and then 1N NaOH (800 mL) was added at room temperature.

Sources & evidence

ORD record
ord-b45e5f7edcba4250ba9ec65e5f3eb41f
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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