HCID 66747614, compound → HCID 66747609, compound

HRID 2279391Notes

Reaction equation

HRID 2279391 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[C@@H:11]([NH:12]C(OCC2C=CC=CC=2)=O)[CH2:10][CH2:9][N:8]([CH2:23][CH2:24][O:25][C:26]2[CH:35]=[N:34][C:33]3[C:28](=[CH:29][C:30]([O:36][CH3:37])=[CH:31][CH:32]=3)[N:27]=2)[CH2:7]1)=[O:5])[CH3:2]>[Pd].CO>[CH2:1]([O:3][C:4]([C@H:6]1[C@@H:11]([NH2:12])[CH2:10][CH2:9][N:8]([CH2:23][CH2:24][O:25][C:26]2[CH:35]=[N:34][C:33]3[C:28](=[CH:29][C:30]([O:36][CH3:37])=[CH:31][CH:32]=3)[N:27]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 66747614HCID 66747614, compound

Product 1

HCID 66747609HCID 66747609, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on activated carbon (188 mg, 0.18 mmol, 0.5 eq) is added at room temperature to a stirred solution of (3R,4S)-4-benzyloxycarbonylamino-1-[2-(7-methoxy-quinoxalin-2-yloxy)-ethyl]-piperidine-3-carboxylic acid ethyl ester (200 mg, 0.35 mmol, 1.0 eq) in methanol (20 mL). The mixture is hydrogenated for 4 hours, then filtered through decalite. Solvent is removed to afford (3R,4S)-4-amino-1-[2-(7-methoxy-quinoxalin-2-yloxy)-ethyl]-piperidine-3-carboxylic acid ethyl ester as a yellow oil (119 mg, 81% yield).

Workup

  1. filtrationfiltered through decalite
  2. customSolvent is removed

Sources & evidence

ORD record
ord-965dbae28a6f4f259c0516355beb924f
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

Loading…