反応 #1702088

反応方程式

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

収率 115.7%

溶媒

DCM

ethyl acetate

反応条件

後処理

1. 1
   洗浄washed sequentially with saturated aqueous sodium bicarbonate, water, and brine
2. 2
   乾燥The organic phase was dried over magnesium sulfate
3. 3
   ろ過filtered
4. 4
   濃縮concentrated
5. 5
   その他The residue was purified by silica gel chromatography (0-10% ethyl acetate:hexanes)

実験手順

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.

出典