反应 #586176

反应方程式

tert-butyl (2-oxoethyl)carbamate

methyl (7R)-14-cyclohexyl-7-(methylamino)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

acetic acid

sodium acetate

→

title compound

收率 82.0%

methyl (7R)-7-[{2-[(tert-butoxycarbonyl)amino]ethyl}(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

收率 82.0%

溶剂

MeOH

methanol

methanol

反应条件

后处理

1. 1
   workup.ADDITIONThe atmosphere in the reaction vessel was charged with H2
2. 2
   workup.STIRRINGthe reaction stirred vigorously under a H2 atmosphere (balloon) at 60° C. overnight
3. 3
   温度to cool to RT
4. 4
   其他flushed with N2
5. 5
   过滤filtered through a plug of CELITE
6. 6
   浓缩The filtrate was concentrated in vacuo
7. 7
   其他the residue purified by FC (PE/EtOAc 2.5:1 to 1.5:1 gradient)

实验过程

To a solution of tert-butyl (2-oxoethyl)carbamate (1 eq; 0.38 M) in dry methanol was added a mixture of methyl (7R)-14-cyclohexyl-7-(methylamino)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.14 M), acetic acid (2 eq) and sodium acetate (1 eq) in dry methanol, and the mixture stirred at RT for 15 min. Then Pd/C (0.3 weight eq) was added as a slurry in MeOH under N2. The atmosphere in the reaction vessel was charged with H2 and the reaction stirred vigorously under a H2 atmosphere (balloon) at 60° C. overnight. The reaction was allowed to cool to RT, flushed with N2 and filtered through a plug of CELITE. The filtrate was concentrated in vacuo and the residue purified by FC (PE/EtOAc 2.5:1 to 1.5:1 gradient) to afford the title compound (82%). (ES+) m/z 562 (M+H)+; [α]D+67.1, c=0.67, CHCl3

来源