ChemicalBook CAS DataBase List 1,3-Dimethyladamantane

1,3-Dimethyladamantane synthesis

12synthesis methods

Product Name:1,3-Dimethyladamantane
CAS Number:702-79-4
Molecular formula:C12H20
Molecular Weight:164.29

941-37-7 Synthesis

941-37-7
419 suppliers
$26.00/5g

702-79-4
464 suppliers
$5.00/1g

Yield:702-79-4 100%

Reaction Conditions:

with 2,2'-azobis(isobutyronitrile);tri-n-butyl-tin hydride at 90; for 1 h;Inert atmosphere;Barton-McCombie Deoxygenation;Solvent;

Steps:

4.6 General procedure for Barton-McCombie radical reduction of compound 5

General procedure: To a solution of thiocarbonate 5g (107 mg, 0.200 mmol) in CPME (0.5 mL) were added dropwise a solution of n-Bu₃SnH (75.7 mg, 0.260 mmol) and AIBN (6.6 mg, 0.040 mmol) in CPME (1.5 mL) with a syringe pump over 30 min at 90 °C. The resultant mixture was stirred at 90 °C for 30 min and concentrated. The residue was purified by 10% w/w K₂CO₃-silica gel flash column chromatography (hexane→hexane/EtOAc=100/1→50/1→20/1) to give the cis-fused cyclized product 6g (53.6 mg, 0.140 mmol, 70%) and 2.8:1 mixture of cis and trans-fused diastereomers (22.0 mg, 0.0572 mmol, 29%). These isomers were separated by the repeated column chromatography for spectral analysis.

References:

Kobayashi, Shoji;Kuroda, Hiroyuki;Ohtsuka, Yuta;Kashihara, Takashi;Masuyama, Araki;Watanabe, Kiyoshi [Tetrahedron,2013,vol. 69,# 10,p. 2251 - 2259]