Gabapentin → HCID 21107358, compound

HRID 389358Notes

Reaction equation

HRID 389358 reaction equation
[CH2:1]1[CH2:6][CH2:5][C:4]([CH2:11][NH2:12])([CH2:7][C:8]([OH:10])=[O:9])[CH2:3][CH2:2]1.[OH-].[CH2:14]([N+:18]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17]>CO>[NH2:12][CH2:11][C:4]1([CH2:7][C:8]([O-:10])=[O:9])[CH2:5][CH2:6][CH2:1][CH2:2][CH2:3]1.[CH2:27]([N+:18]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 3446GabapentinHCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 21107358HCID 21107358, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution containing gabapentin (34.4 g, 200 mmol), a 1 M solution of tetrabutylammonium hydroxide in methanol (200 mL, 200 mmol), and additional methanol (200 mL) was stirred at ambient temperature for 14 h. The solvent was removed in vacuo, then toluene (200 mL) was added and evaporated under reduced pressure two times. The title compound (11) was obtained as a thick syrup, and was further dried under high vacuum and used without further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. additiontoluene (200 mL) was added
  3. customevaporated under reduced pressure two times

Sources & evidence

ORD record
ord-9da23056fd224cbeafda48ec16e78cb9
Source dataset
uspto-grants-2013_02
Patent number
US08378137B2

Reaction notes

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