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METHYL 4-HYDROXYADAMANTAN-1-CARBOXYLATE synthesis

3synthesis methods
81968-77-6 Synthesis
4α-Hydroxyadamantane-1-carboxylic acid

81968-77-6
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Yield:81968-76-5 84%

Reaction Conditions:

with hydrogenchloride in 1,4-dioxane at 20; for 48 h;

Steps:

3.2

Step 2; To a stirred solution of 4-hydroxyadamantane-1-carboxylic acid (4.47 g, 22.8 mmol) in MeOH (75 mL) was added 4 M HCl in dioxane (25 mL, 100 mmol). The mixture was stirred at rt for 2 d and concentrated. The residue was purified by chromatography on a 40-g silica cartridge eluted with a 0-80% EtOAc in hexanes gradient to afford methyl 4-hydroxyadamantane-1-carboxylate (4.04 g, 84%) as a clear, colorless oil.

References:

US2011/34455,2011,A1 Location in patent:Page/Page column 33-34