Gabapentin → HCID 21107358, compound

HRID 530223Notes

Reaction equation

HRID 530223 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-b4549b1b00dc452eb793b2a57890c983
Source dataset
uspto-grants-2016_05
Patent number
US09353057B2

Reaction notes

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