Реакция #44780

Уравнение реакции

sodium triacetoxyborohydride

sodium bicarbonate

N-Boc nortropinone

methyl 4-aminomethylbenzoate

acetic acid

→

1,1-dimethylethyl 3-[[[4-(methoxycarbonyl)phenyl]methyl]amino]-8-azabicyclo[3.2.1]octane-8-carboxylate

Выход 88.2%

Растворители

dichloroethane

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   Экстракцияextracted with ethyl acetate (2×)
3. 3
   ДругоеThe combined organic extracts were dried
4. 4
   Концентрированиеconcentrated
5. 5
   ДругоеPurification by flash chromatography on silica gel using a gradient of ethyl acetate in hexane

Методика

A solution of N-Boc nortropinone (2.4 g, 10.9 mmol) and methyl 4-aminomethylbenzoate (1.6 g, 10.9 mmol) in dichloroethane (20 mL) was stirred as acetic acid (0.85 g, 14.2 mmol) was added. After 1 hour, sodium triacetoxyborohydride (2.7 g, 13.1 mmol) was added and the reaction was stirred for 17 hours. The reaction was treated with a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate (2×). The combined organic extracts were dried and concentrated. Purification by flash chromatography on silica gel using a gradient of ethyl acetate in hexane gave 3.6 g of 1,1-dimethylethyl 3-[[[4-(methoxycarbonyl)phenyl]methyl]amino]-8-azabicyclo[3.2.1]octane-8-carboxylate.

Источник