Isobutylamine → Piperlonguminine

온도

0 °C

A mixture of piperinic acid (350 mg, 0.0016 mole, 1 eq) and triethylamine (0.4 ml, 0.0032 mole, 2 eq) in dichloromethane (50 ml) was stirred for 15 min at 0° C. To this mixture methanesulfonyl chloride (0.18 ml, 0.0024 mole, 1.5 eq) was added and stirred for further 30 min at 0° C. Isobutylamine (0.23 ml, 0.0024 mole, 1.5 eq) was added to the mixture and stirred for 1 h at 0° C. and 2 h at room temperature. Dichloromethane (50 ml) was added to the mixture which was then washed with 5% HCl (3×100 ml), saturated aqueous NaHCO3 (3×100 ml) and water (3×100 ml). The organic fraction was dried over anhydrous sodium sulphate, filtered and rotary evaporated to yield a yellowish solid residue. Recrystallisation from methanol yielded colourless needles of piperlonguminine (120 mg, 32% yield)2. The reaction is presumed to proceed through a mesylate ester intermediate.

1. stirringstirred for further 30 min at 0° C
2. stirringstirred for 1 h at 0° C. and 2 h at room temperature
3. washwas then washed with 5% HCl (3×100 ml), saturated aqueous NaHCO3 (3×100 ml) and water (3×100 ml)
4. dry with materialThe organic fraction was dried over anhydrous sodium sulphate
5. filtrationfiltered
6. customrotary evaporated
7. customto yield a yellowish solid residue

ORD 기록

ord-871b70a645d14e6aa97d46114f3d33de

출처 데이터셋

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06680391B2