Ammonium Hydroxide → Gabapentin

HRID 1862586Notes

Reaction equation

HRID 1862586 reaction equation
C([O:8][C:9](=[O:19])[CH2:10][C:11]1([C:17]#[N:18])[CH:16]=[CH:15][CH2:14][CH:13]=[CH:12]1)C1C=CC=CC=1.[NH4+].[OH-]>[Pd].CO>[NH2:18][CH2:17][C:11]1([CH2:10][C:9]([OH:19])=[O:8])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 54210642HCID 54210642, compound

Product 1

HCID 3446GabapentinYield 93.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Added 5% Pd/C catalyst (0.84 g, 0.40 mmol) to a solution of (1-cyanocyclohexa-2,5-dienyl)acetic acid benzyl ester (1.00 g, 3.95 mmol) and 28% NH4OH (0.55 mL, 0.50 g, 4.0 mmol) in MeOH (20 mL). After shaking the reaction mixture under 50 psi H2 at 50° C. for 18 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 0.63 g (93%) 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-2ae32621db334a6b8406e5bf794da8cf
Source dataset
uspto-grants-2003_03
Patent number
US06538148B2

Reaction notes

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