反応 #66731

反応方程式

(4-Oxo-adamantan-1-yl)-carbamic acid benzyl ester

sodium borohydride

HCl

→

desired product

収率 53.2%

(4-Hydroxy-adamantan-1-yl)-carbamic acid benzyl ester

収率 53.2%

溶媒

THF

反応条件

後処理

1. 1
   抽出The reaction mixture was extracted three times with ethyl acetate
2. 2
   乾燥the combined organic layer was dried over sodium sulphate
3. 3
   その他evaporated
4. 4
   その他The resulting oil was subjected to HPLC separation

実験手順

865 mg of (4-Oxo-adamantan-1-yl)-carbamic acid benzyl ester (12) were dissolved in 15 mL of THF and 109 mg of sodium borohydride were added at 0° C. Stirring was continued for 2 h, then the reaction mixture was acidified by addition of 2M HCl. The reaction mixture was extracted three times with ethyl acetate and the combined organic layer was dried over sodium sulphate and evaporated. The resulting oil was subjected to HPLC separation to give 463 mg of the desired product as a cis/trans mixture along with 119 mg of the cis derivative (13a) and 10 mg of the trans derivative (13b). 13a: Rt=1.37 min (Method 3). Detected mass: 302.3 (M+H+). 13b: Rt=1.39 min (Method 3). Detected mass: 302.3 (M+H+);

出典