HCID 68283984, compound → HCID 68283597, compound

HRID 1527402Notes

Reaction equation

HRID 1527402 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@:11]([F:14])([CH3:13])[CH2:10][C@H:9]1[C:15]([O:17]CC1C=CC=CC=1)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@:11]([F:14])([CH3:13])[CH2:10][C@H:9]1[C:15]([OH:17])=[O:16])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 68283984HCID 68283984, compound

Product 1

HCID 68283597HCID 68283597, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution containing (2S,4R)-4-fluoro-4-methyl-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (700 mg, 2.075 mmol) and Pd/C 10% (221 mg, 2.075 mmol) in THF (6 mL) was placed under a nitrogen atmosphere and stirred for 5 h. The catalyst was removed through a pad of celite and washed with MeOH. Solvents were removed under vacuum to give the desired material as a colorless oil which was used without further purification in the next step. MS (UPLC/MS): 246.2 [M−H]−, 292.2 [M+HCOO−]−, 493.4 [2M−H]−.

Workup

  1. customThe catalyst was removed through a pad of celite
  2. washwashed with MeOH
  3. customSolvents were removed under vacuum

Sources & evidence

ORD record
ord-3d0557d421384d319b716f17e036ec66
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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