HCID 69914328, compound → Gabapentin

HRID 1884595Notes

Reaction equation

HRID 1884595 reaction equation
[N+:1]([CH2:4][C:5]1([CH2:11][C:12]([O:14]CC2C=CC=CC=2)=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][CH2:4][C:5]1([CH2:11][C:12]([OH:14])=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 69914328HCID 69914328, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 3446Gabapentin

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of 5 g (0.017 mol) of benzyl 1-(nitromethyl)cyclohexyl-acetate in 50 ml of methanol is added to a mixture of 0.5 g of prehydrogenated palladium, 10% on activated carbon in 50 ml of methanol. This mixture is hydrogenated at room temperature under atmospheric pressure until the calculated hydrogen is consumed, then the catalyst is filtered off, the filtrate is concentrated to about 15 ml and 30 ml of tetrahydrofuran is added to precipitate the title compound. Yield: 1.5 g (51%). Mp: 168° C.

Workup

  1. customis consumed
  2. filtrationthe catalyst is filtered off
  3. concentrationthe filtrate is concentrated to about 15 ml and 30 ml of tetrahydrofuran
  4. additionis added
  5. customto precipitate the title compound

Sources & evidence

ORD record
ord-efc38315ce8041c9b190da61e56a6c84
Source dataset
uspto-grants-2004_07
Patent number
US06765114B1

Reaction notes

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