Benzyl Alcohol → 4-Piperidinecarboxylic acid, phenylmethyl ester

反応式

S(Cl)(Cl)=O.[NH:5]1[CH2:10][CH2:9][CH:8]([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]1.[CH2:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([O:12][C:11]([CH:8]1[CH2:9][CH2:10][NH:5][CH2:6][CH2:7]1)=[O:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

反応物 3

HCID 244Benzyl Alcohol

HCID 37734-Piperidinecarboxylic acid

HCID 24386Thionyl Chloride

生成物 1

HCID 114133364-Piperidinecarboxylic acid, phenylmethyl ester収率 97.25%

実験手順

Thionyl chloride (5.42 g, 46 mmol) was added to a cold (0-4° C.) stirred solution piperidine-4-carboxylic acid (5 g, 38.7 mmol) in benzyl alcohol (150 mL) and stirring was continued overnight. Benzyl alcohol was removed by stirring with hexane, ether and decanting the solvent, dried to afford 8.26 g (97.25% yield) of piperidine-4-carboxylic acid benzyl ester. LCMS Purity: 94.8%.