Ammonium Hydroxide → Gabapentin

HRID 1862585Notes

Reaction equation

HRID 1862585 reaction equation
[C:1]([C:3]1([CH2:9][C:10]([OH:12])=[O:11])[CH:8]=[CH:7][CH2:6][CH:5]=[CH:4]1)#[N:2].[NH4+].[OH-]>[Pd].CO>[NH2:2][CH2:1][C:3]1([CH2:9][C:10]([OH:12])=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 18620044HCID 18620044, compound

Product 1

HCID 3446GabapentinYield 105.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Added 5% Pd/C catalyst (0.33 g, 0.16 mmol) to a solution of (1-cyanocyclohexa-2,5-dienyl)acetic acid (0.25 g, 1.5 mmol) and 28% NH4OH (70 μL, 63 μg, 0.50 mmol) in MeOH (20 mL). After shaking the reaction mixture under 50 psi H2 at 50° C. for 3.5 hours, the pressure was slowly released, and the reaction was cooled to room temperature. The reaction was filtered and concentrated under reduced pressure to afford 0.27 g (102%) of crude product.

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-02492d15318741d0a30689a74fce5394
Source dataset
uspto-grants-2003_03
Patent number
US06538148B2

Reaction notes

Loading…