반응 #1702088

반응 방정식

3-amino-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester, hydrochloride salt

3-benzyloxy-cyclobutanone

sodium triacetoxyborohydride

→

3-(3-benzyloxy-cyclobutylamino)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester

수율 115.7%

용매

DCM

ethyl acetate

반응 조건

후처리

1. 1
   세척washed sequentially with saturated aqueous sodium bicarbonate, water, and brine
2. 2
   건조The organic phase was dried over magnesium sulfate
3. 3
   여과filtered
4. 4
   농축concentrated
5. 5
   기타The residue was purified by silica gel chromatography (0-10% ethyl acetate:hexanes)

실험 절차

A mixture of 3-amino-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester, hydrochloride salt (750 mg, 2.74 mmol) and 3-benzyloxy-cyclobutanone (2.5 g, 14.3 mmol) in DCM (40 mL) was treated with sodium triacetoxyborohydride (3.34 g, 15.8 mmol) portionwise. The mixture was stirred at room temperature for 3 hours. The solution was diluted with ethyl acetate, washed sequentially with saturated aqueous sodium bicarbonate, water, and brine. The organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (0-10% ethyl acetate:hexanes). This resulted in 1.26 g (quant. yield) of 3-(3-benzyloxy-cyclobutylamino)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester as a mixture of cis- and trans-isomers.

출처