(2-Methylpropyl)boronic acid → (3aS,4S,6S,7aR)-3a,5,5-Trimethyl-2-(2-methylpropyl)hexahydro-2H-4,6-methano-1,3,2-benzodioxaborole

HRID 556291노트

반응식

HRID 556291 반응식
[C:1]12(O)[CH2:9][CH:5]([C:6]1([CH3:8])[CH3:7])[CH2:4][CH2:3][C:2]2([OH:11])[CH3:10].[CH3:13][CH:14]([CH3:19])[CH2:15][B:16](O)[OH:17]>C(OCC)C>[CH3:13][CH:14]([CH3:19])[CH2:15][B:16]1[O:17][C@@H:3]2[CH2:4][C@@H:5]3[CH2:9][C@H:1]([C@:2]2([CH3:10])[O:11]1)[C:6]3([CH3:8])[CH3:7]

참가 물질

4

반응물 2

HCID 2734395(2-Methylpropyl)boronic acidHCID 219250472,6,6-Trimethylbicyclo[3.1.1]heptane-1,2-diol

생성물 1

HCID 12842239(3aS,4S,6S,7aR)-3a,5,5-Trimethyl-2-(2-methylpropyl)hexahydro-2H-4,6-methano-1,3,2-benzodioxaborole수율 98.6%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

A mixture of (+)-pinanediol (23.9 g, 0.140 mol) and 2-methylpropylboronic acid (15 g, 0.147 mol) in diethyl ether (300 ml) was stirred at room temperature for 24 h. The mixture was dried over anhydrous sodium sulfate and purified by column chromatography (Silica gel 230-400 mesh), eluting with hexane:ethyl acetate 90:10 mixture. The product was obtained as a clear oil (32.6 g, 94% yield).

후처리

  1. dry with materialThe mixture was dried over anhydrous sodium sulfate
  2. custompurified by column chromatography (Silica gel 230-400 mesh)
  3. washeluting with hexane:ethyl acetate 90:10 mixture

출처 및 근거

ORD 기록
ord-51f8872fc3424168b81e81382e43e680
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058262B2

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