2-benzyl 1-tert-butyl (2R,3S)-3-fluoropyrrolidine-1,2-dicarboxylate → (2R,3S)-1-(tert-Butoxycarbonyl)-3-fluoropyrrolidine-2-carboxylic acid

HRID 1527326Notes

Reaction equation

HRID 1527326 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([F:13])[C@H:9]1[C:14]([O:16]CC1C=CC=CC=1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([F:13])[C@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 155475702-benzyl 1-tert-butyl (2R,3S)-3-fluoropyrrolidine-1,2-dicarboxylate

Product 1

HCID 15547566(2R,3S)-1-(tert-Butoxycarbonyl)-3-fluoropyrrolidine-2-carboxylic acidYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (2R,3S)-3-fluoro-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (252 mg, 0.778 mmol; 72% purity by HPLC/215 nm) in MeOH (20 mL) was hydrogenated at RT (1 atm) over Pd/C 10% (35 mg, 10% w/w) for 24 h. The reaction mixture was filtered through a 0.45 microns filter and concentrated under reduced pressure to give the crude title compound (70% purity by HPLC/215 nm) as a white solid. This material was used in the next reaction step without further purification. MS (LC/MS): 232 [M−H]+; tR (HPLC conditions b): 2.78 min.

Workup

  1. customwas hydrogenated at RT
  2. customfor 24 h
  3. filtrationThe reaction mixture was filtered through a 0.45 microns
  4. filtrationfilter
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-951dec348a3b4a2b9b462e3580cb73e9
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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