반응 #1295

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(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

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   기타quenched with aqueous ammonium chloride
2. 2
   workup.ADDITIONdiluted with water
3. 3
   추출extracted twice with ethyl acetate
4. 4
   세척The combined organic layers were washed with brine
5. 5
   건조dried (sodium sulfate)
6. 6
   여과filtered
7. 7
   농축concentrated to a yellow oil
8. 8
   세척eluting with 2:1 hexane/ethyl acetate, 750 mg

실험 절차

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.

출처