(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 1037732ノート

反応式

HRID 1037732 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3c433a54df0445fb9c4c4b0e399bd591
出典データセット
uspto-grants-2013_10
特許番号
US08546608B2

反応ノート

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