2,2-Dimethylpropionic acid 2-[(S)-3-(5-fluoro-2-nitrophenylamino)piperidin-1-yl]ethyl ester → 2,2-Dimethylpropionic acid 2-[(S)-3-(2-amino-5-fluorophenylamino)piperidin-1-yl]ethyl ester

HRID 243034Notes

Reaction equation

HRID 243034 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:24]([O-])=O)=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][CH2:16][O:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:10]2)[CH:7]=1>[Pd]>[NH2:24][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:6]=1[NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][CH2:16][O:17][C:18](=[O:23])[C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:10]1

Participants

3

Reactant 1

HCID 681569292,2-Dimethylpropionic acid 2-[(S)-3-(5-fluoro-2-nitrophenylamino)piperidin-1-yl]ethyl ester

Product 1

HCID 681574342,2-Dimethylpropionic acid 2-[(S)-3-(2-amino-5-fluorophenylamino)piperidin-1-yl]ethyl ester

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 2,2-dimethylpropionic acid 2-[(S)-3-(5-fluoro-2-nitrophenylamino)piperidin-1-yl]ethyl ester (2.3 g, 6.26 mmol) in EtOAC (100 mL) was added a slurry of 10% Pd/C (200 mg) in IMS (20 mL) and the reaction mixture stirred at RT under a hydrogen atmosphere for 24 h. The suspension was filtered through a pad of Celite® and the filtrate concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 2-6% 2M NH3/MeOH in DCM) affording the title compound as a colourless gum affording the title compound as a dark red oil (1.464 g, 69%). LCMS (Method J): RT 1.71 min [M+H]+ 338.

Workup

  1. filtrationThe suspension was filtered through a pad of Celite®
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 2-6% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-15397b4b9a7b4b319e4190030bdda717
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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