(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 589316Notes

Reaction equation

HRID 589316 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1f60df9dbf614353a388bf73963703e3
Source dataset
uspto-grants-2016_01
Patent number
US09233115B2

Reaction notes

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