Reaction #48494

Reaction equation

sodium hydroxide

benzyl 4-oxopiperidin-1-carboxylate

2-aminoethanol

sodium triacetoxyborohydride

→

title compound

Yield 107.7%

Benzyl 4-[ (2-hydroxyethyl)amino]piperidin-1-carboxylate

Yield 107.7%

Solvents

1,2-dichloroethane

methanol

acetic acid

Conditions

Workup

1. 1
   Otherthe organic layer was separated
2. 2
   DryingThe organic layer was dried over anhydrous sodium sulfate
3. 3
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure

Procedure

A solution of benzyl 4-oxopiperidin-1-carboxylate (7.0 g), 2-aminoethanol (2.8 g) and acetic acid (2.7 g) in 1,2-dichloroethane (150 mL)-methanol (10 mL) was stirred at room temperature for 3 hours, sodium triacetoxyborohydride (12.7 g) was added thereto, and the mixture was stirred at room temperature for 15 hours. A 1N sodium hydroxide solution was added to the reaction mixture, pH of the aqueous layer was adjusted to about 12, and then the organic layer was separated. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound (9.0 g, quantitative) as a colorless oil.

Source