1-(4-METHOXY-BENZYL)-5-OXO-PYRROLIDINE-3-CARBOXYLIC ACID synthesis

5synthesis methods

Product Name:1-(4-METHOXY-BENZYL)-5-OXO-PYRROLIDINE-3-CARBOXYLIC ACID
CAS Number:96449-89-7
Molecular formula:C13H15NO4
Molecular Weight:249.26

149505-71-5 Synthesis

Methyl 1-(4-Methoxybenzyl)-5-oxopyrrolidine-3-carboxylate

149505-71-5
29 suppliers
$45.00/50mg

1-(4-METHOXY-BENZYL)-5-OXO-PYRROLIDINE-3-CARBOXYLIC ACID

96449-89-7
35 suppliers
$55.00/250mg

Yield:96449-89-7 93%

Reaction Conditions:

with water;potassium hydroxide in tetrahydrofuran at 20; for 0.5 h;

Steps:

1-(4-Methoxybenzyl)-5-oxopyrrolidine-3-carboxylic acid (5a)

A solution of compound 4a (1.84 g; 7 mmol) in THF (10 mL) was dissolved in 10 mL THF was treated with 10% KOH (10 mL) at room temperature for 30 min. THF was removed and the residue was acidified with 6 N HCl to pH 2, then extracted with ethyl acetate (2 x 15 mL). The combined organic layers were washed with brine (2 x 15 mL) and dried over anhydrous sodium sulfate. The solvent was removed to give compound 5a as a white solid (1.62 g; 93% yield), mp 150-151 ^oC. ¹H NMR (Acetone-d₆): δ 2.62 (d, J = 8.7 Hz, 2H), 3.22-3.35 (m, 1H), 3.41-3.58 (m, 2H), 3.78 (s, 3H), 4.37 (dd, J = 30.4, 13.9 Hz, 2H), 6.89 (d, J = 8.3 Hz, 2H), 7.20 (d, J = 8.3 Hz, 2H).

References:

Dou, Dengfeng;He, Guijia;Mandadapu, Sivakoteswara Rao;Aravapalli, Sridhar;Kim, Yunjeong;Chang, Kyeong-Ok;Groutas, William C. [Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,# 1,p. 377 - 379] Location in patent:supporting information; experimental part

97-65-4 Synthesis