HCID 11065077, compound → Gabapentin

HRID 846406Notes

Reaction equation

HRID 846406 reaction equation
C([O:8][C:9](=[O:19])[CH2:10][C:11]1([C:17]#[N:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)C1C=CC=CC=1.[H][H]>CO.[Rh]>[CH2:14]1[CH2:13][CH2:12][C:11]([CH2:17][NH2:18])([CH2:10][C:9]([OH:19])=[O:8])[CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 11065077HCID 11065077, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 3446GabapentinYield 27.7%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

1.0 g (3.8 mmol) of (1-cyanocyclohexyl)acetic acid benzyl ester was distilled in 20 ml of methanol, mixed with 0.2 g of Rh/C 5 percent and hydrogenated at 10 bars of hydrogen pressure. After 23 hours at room temperature the suspension was filtered, the filtrate was concentrated to 3 ml, mixed with 25 ml of ethanol, concentrated to 4 ml and put on the cooling shelf. The precipitated product was filtered, washed with ethanol and dried. 0.18 g of Gabapentin was obtained, corresponding to a yield of 27 percent (relative to the (1-cyanocyclohexyl)acetic acid benzyl ester used). Data for the product was:

Workup

  1. filtrationAfter 23 hours at room temperature the suspension was filtered
  2. concentrationthe filtrate was concentrated to 3 ml
  3. additionmixed with 25 ml of ethanol
  4. concentrationconcentrated to 4 ml
  5. filtrationThe precipitated product was filtered
  6. washwashed with ethanol
  7. customdried

Sources & evidence

ORD record
ord-bb40e21d33654d7782e866e46fb35e94
Source dataset
uspto-grants-1992_08
Patent number
US05136091

Reaction notes

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