ChemicalBook CAS DataBase List Gabapentin

Gabapentin synthesis

8synthesis methods

Product Name:Gabapentin
CAS Number:60142-96-3
Molecular formula:C9H17NO2
Molecular Weight:171.24

In the original synthesis (Goedecke) cyclohexenone is reacted with ethyl cyanoacetate in the presence of ammonia to yield the Guareschi salt, which is hydrolyzed and decarboxylated to give 1,1-cyclohexanediacetic acid which is transformed by to the corresponding anhydride with acetic anhydride. This anhydride is treated with methanol to yield the half ester 2- acetic acid, which is subjected to a Curtius type rearrangement to give the isocyanate 2-acetic acid. The desired compound is obtained by hydrolysis of 2-acetic acid with HCl, followed by hydrochloric salt removal via anion exchange .
Synthesis_60142-96-3

3396-14-3
70 suppliers
$183.00/250mg

60142-96-3
767 suppliers
$9.34/5g

Yield:60142-96-3 98%

Reaction Conditions:

in tetrahydrofuran;water;

Steps:

39.39 Synthesis of Compound 1

Example 39 Synthesis of Compound 1 Lithium aluminum hydride (69.4 mL of a 1 M solution in ether, 69.4 mmol) was added dropwise to a stirring solution of cis-cyclobutane-1,2-dicarboxylic acid (5 g, 34.7 mmol) in THF (60 mL) at 0° C. under argon. The mixture was allowed to warm to room temperature and stirred for 16 hours. The mixture was cooled to 0° C. and quenched by careful addition of water (2.7 mL), sodium hydroxide solution (2.7 mL of a 15% w/v solution), and water (8.1 mL). The mixture was stirred for 15 minutes, and the precipitate was removed by filtration. The solvent was evaporated under reduced pressure to give the alcohol 1 as a colorless oil (4.0 g, 98%); δ_H (400 MHz; CDCl₃): 3.85 (2H, m), 3.6 (2H, m), 3.2 (2H, s), 2.7 (2H, m), 2 (2H, m); 1.55 (2H, m); δ_C (400 MHz; CDCl₃): 63.15, 37.83, 20.40.

References:

US2002/72533,2002,A1