ChemicalBook CAS DataBase List 1-(tert-Butyl)3-methylbicyclo[1.1.1]pentane-1,3-dicarboxylate

1-(tert-Butyl)3-methylbicyclo[1.1.1]pentane-1,3-dicarboxylate synthesis

3synthesis methods

Product Name:1-(tert-Butyl)3-methylbicyclo[1.1.1]pentane-1,3-dicarboxylate
CAS Number:138732-31-7
Molecular formula:C12H18O4
Molecular Weight:226.27

24424-99-5 Synthesis

24424-99-5
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83249-10-9 Synthesis

Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid, MonoMethyl ester

83249-10-9
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1-(tert-Butyl)3-methylbicyclo[1.1.1]pentane-1,3-dicarboxylate

138732-31-7
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$649.00/250mg

Yield:-

Reaction Conditions:

with dmap in tert-butyl alcohol at 20; for 72 h;Inert atmosphere;

Steps:

195 5-((3-(5-(2,5-Difluoro-4-methylphenyl)-4,5-dihydro-1H-pyrazole-1-carbonyl)bicyclo[1.1.1]pentan-1-yl)methoxy)pyrazine-2-carbonitrile

1-(tert-Butyl) 3-methyl bicyclo[1.1.1]pentane-1,3-dicarboxylate To a flask containing 3-(methoxycarbonyl)bicyclo[1.1.1]pentane-1-carboxylic acid (24.7 g, 145 mmol), DMAP (5.32 g, 43.5 mmol) and Boc₂O (67.4 ml, 290 mmol) was added tBuOH (97 ml), and the mixture was stirred at rt.
The reaction was vented under a stream of N₂, and after the evolution of gas abated, the reaction was stirred for 3 d, by which time material solidified.
The reaction was diluted with CH₂Cl₂ and concentrated, then diluted with Et₂O (100 ml) and washed with aqueous citric acid (250 ml, 10%), aqueous NaOH (250 ml, 0.1 M), and brine.
Each aqueous layer was extracted with the same Et₂O (2*125 ml).
The organic layers were combined, dried over MgSO₄, and concentrated, and residual tBuOH was azeotroped from CH₂Cl₂/Hexanes to give the title compound (42.7 g, 181 mmol, 125% yield) as a white waxy solid that contained 11 mole % tBuOH, and the title compound 96% pure. The material was carried on to the next step without further purification. ¹H NMR (500 MHz, DMSO-d₆) δ 3.61 (s, 3H), 2.19 (s, 6H), 1.40 (s, 9H).

References:

US2021/94921,2021,A1 Location in patent:Paragraph 0842-0845

83249-10-9 Synthesis

83249-10-9
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$24.00/100mg

138732-31-7
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$649.00/250mg

References

Bicyclo[1.1.1]pentane-1-carboxylic acid, 3-(chlorocarbonyl)-, methyl ester

110371-22-7
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75-65-0 Synthesis

75-65-0
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$10.00/10ml

138732-31-7
24 suppliers
$649.00/250mg

References