5-Aminovaleric acid → Methyl 5-aminopentanoate

Participants

Reaction Steps

Methanol (15 mL) was cooled to 0° C., combined with thionyl chloride (1.25 mL, 17.1 mmol) and stirred further for 30 minutes. This reaction solution was combined with 5-amino-n-valeric acid (500 mg, 4.3 mmol) and stirred at room temperature overnight. After completion of the reaction, the mixture was concentrated under reduced pressure to obtain a residue, which was dissolved in methylene chloride (10 mL), combined with 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (1.85 g, 6.4 mmol) and stirred overnight. The reaction solution was concentrated under reduced pressure, and the residue was subjected to a column chromatography to obtain 5-amino-n-valeric acid methyl ester (compound 102; yield: 865 mg).

Provenance & Evidence