تفاعل #8852

معادلة التفاعل

ammonium chloride

propionaldehyde

tert-butyl 4-acetyl-4-methoxypiperidine-1-carboxylate

tert-Butyl 4-acetyl-4-methoxypiperidine-1-carboxylate

lithium diisopropylamine

→

title compound

المردود 55.9%

tert-Butyl 4-(3-hydroxy-1-oxopent-1-yl)-4-methoxypiperidine-1-carboxylate

المردود 55.9%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted three times with diethyl ether
2. 2
   غسيلwashed with saturated sodium chloride solution
3. 3
   تجفيفdried over sodium sulfite
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated
6. 6
   أخرىThe residue was purified by flash chromatography
7. 7
   غسيلeluting with 40% ethyl acetate/hexanes

الإجراء التجريبي

To a solution of tert-butyl 4-acetyl-4-methoxypiperidine-1-carboxylate (0.589 g, 2.29 mmol) from Step A in tetrahydrofuran (20 mL) at −78° C. was added lithium diisopropylamine (0.650 mL, 0.974 mmol) followed by propionaldehyde (0.266 g, 0.330 mL, 4.58 mmol). After 5 min, the reaction mixture was poured into saturated ammonium chloride, and extracted three times with diethyl ether. The organic layers were combined, washed with saturated sodium chloride solution, dried over sodium sulfite, filtered, and concentrated. The residue was purified by flash chromatography eluting with 40% ethyl acetate/hexanes to afford the title compound (0.404 g). MS/EI (acetonitrile/water): m/z 216.1 (M+1−BOC) retention time=2.69 min.

المصدر