5-(hydroxyMethyl)-1-Methylpyrrolidin-2-one synthesis

Yield: 75%

Reaction Conditions:

with sodium hydroxide;lithium aluminium tetrahydride in tetrahydrofuran;water

Steps:

1.B B.
To a mechanically-stirred -78° C. solution of 5(R)- or 5(S)-carbomethoxy-1-methyl-2pyrrolidinone (22.0 g; 0.140 mol) in dry THF (400 mL) under an atmosphere of nitrogen was added a solution of LAH (70 ml of a 1.0 M solution in THF; 70 mmol) dropwise over a period of 20 min. After being stirred for 1 hr. at -78° C., the cooling bath was removed and the stirring was continued for another 1.5 hr at which time the reaction was quenched by the addition of 7 mL of 10% aqueous NaOH solution, followed by 7 mL of water. The resulting mixture was stirred for 2 hr., until a white precipitate had formed. This precipitate was removed by filtration and was washed with EtOAc, with the filtrate solvents being removed under reduced pressure. The resulting oil was purified by flash chromatography (SiO₂; 3%-7% MeOH/CH₂ Cl₂) to obtain 5-hydroxymethyl-1-methyl-2-pyrrolidinone as a colorless oil (13.5 g; 75% yield).

References:

Merck & Co., Inc. US5006511, 1991, A