HuagongsheHuagongshe Chemistry Print Report · For research reference only
(2-Methylpropyl)boronic acid → (3aS,4S,6S,7aR)-3a,5,5-Trimethyl-2-(2-methylpropyl)hexahydro-2H-4,6-methano-1,3,2-benzodioxaborole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (2-Methylpropyl)boronic acid | HCID 2734395 | — |
| Reactant | 2,6,6-Trimethylbicyclo[3.1.1]heptane-1,2-diol | HCID 21925047 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | (3aS,4S,6S,7aR)-3a,5,5-Trimethyl-2-(2-methylpropyl)hexahydro-2H-4,6-methano-1,3,2-benzodioxaborole | HCID 12842239 | 98.6% |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08283367B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-a05dd8ba51d14d8da22061862a88a5be |
| Source note | uspto-grants-2012_10 |