反应 #1295

反应方程式

(3S-cis)-hexahydro-3-[[(1,1-dimethylethoxy)carbonyl]amino]-7-methyl-2H-azepin-2-one

lithium bis(trimethylsilyl)amide

ethyl bromoacetate

→

title product

(3S-cis)-Hexahydro-3-[[(1,1-dimethylethoxy)-carbonyl]amino]-7-methyl-2-oxo-1H-azepine-1-acetic acid, ethyl ester

溶剂

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   其他quenched with aqueous ammonium chloride
2. 2
   workup.ADDITIONdiluted with water
3. 3
   萃取extracted twice with ethyl acetate
4. 4
   洗涤The combined organic layers were washed with brine
5. 5
   干燥dried (sodium sulfate)
6. 6
   过滤filtered
7. 7
   浓缩concentrated to a yellow oil
8. 8
   洗涤eluting with 2:1 hexane/ethyl acetate, 750 mg

实验过程

A solution of (3S-cis)-hexahydro-3-[[(1,1-dimethylethoxy)carbonyl]amino]-7-methyl-2H-azepin-2-one [prepared as described in Example 64(f), 500 mg., 2.06 mmol.] in tetrahydrofuran (13 ml.) at room temperature under argon was treated dropwise with 1.0M lithium bis(trimethylsilyl)amide in tetrahydrofuran (2.7 ml., 2.7 mmol.) immediately followed by the dropwise addition of ethyl bromoacetate (0.47 ml., 4.21 mmol.). The resulting mixture was stirred for 30 minutes, quenched with aqueous ammonium chloride, diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried (sodium sulfate), filtered and concentrated to a yellow oil. Following flash chromatography (E Merck silica gel) eluting with 2:1 hexane/ethyl acetate, 750 mg. of title product was obtained as a light yellow oil; TLC (1:1 ethyl acetate:hexane) Rf =0.52.

来源