反応 #1431

反応方程式

(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

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   その他quenched with aqueous ammonium chloride
2. 2
   workup.ADDITIONdiluted with water
3. 3
   抽出extracted twice with ethyl acetate
4. 4
   洗浄The combined organic layers were washed with brine
5. 5
   乾燥dried (sodium sulfate)
6. 6
   ろ過filtered
7. 7
   濃縮concentrated to a yellow oil
8. 8
   洗浄eluting with 2:1 hexane/ethyl acetate, 750 mg

実験手順

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.

出典