Ammonia → Gabapentin

HRID 1868431Notes

Reaction equation

HRID 1868431 reaction equation
[Li].N.CCOC(CBr)=O.[C:10]([C:12]1([CH2:18][C:19]([OH:21])=[O:20])[CH:17]=[CH:16][CH2:15][CH:14]=[CH:13]1)#[N:11].[H][H]>[OH-].[NH4+].[Pd].C(#N)C1C=CC=CC=1>[CH2:15]1[CH2:14][CH2:13][C:12]([CH2:10][NH2:11])([CH2:18][C:19]([OH:21])=[O:20])[CH2:17][CH2:16]1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 7748Ethyl bromoacetateHCID 3028194LithiumHCID 18620044HCID 18620044, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 3446Gabapentin

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 7505BenzonitrileSolventHCID 14923Ammonium HydroxideSolvent

Procedure

In U.S. Pat. No. 6,294,690, benzo nitrile was subjected to a Birch reduction with lithium and liquid ammonia and the reduction intermediates trapped with ethyl bromo acetate. The resultant product was hydrolysed to (1-cyano cyclo hexa-2,5-dienyl) acetic acid which was hydrogenated in methanolic ammonium hydroxide for 3.5 hrs at 50 deg C. and 50 psi hydrogen pressure and on 5% palladium charcoal catalyst. The mixture was filtered and the filtrate concentrated to give crude gabapentin.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-0e5e1c1d1f7a4148a7027112d76147fd
Source dataset
uspto-grants-2009_12
Patent number
US07635717B2

Reaction notes

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