endo-8-Azabicyclo[3.2.1]octane-3,8-dicarboxylic acid, 8-(1,1-dimethylethyl) 3-methyl ester synthesis
- Product Name:endo-8-Azabicyclo[3.2.1]octane-3,8-dicarboxylic acid, 8-(1,1-dimethylethyl) 3-methyl ester
- CAS Number:1548548-51-1
- Molecular formula:C14H23NO4
- Molecular Weight:269.34
67-56-1
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![8-Azabicyclo[3.2.1]octane-3,8-dicarboxylic acid, 8-(1,1-diMethylethyl) ester, (3-endo)-](/CAS/GIF/1222996-05-5.gif)
1222996-05-5
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1548548-51-1
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Yield:-
Reaction Conditions:
with dmap;1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;N-ethyl-N,N-diisopropylamine in dichloromethane at 20; for 16 h;
Steps:
33A.A; 33B.A Step A: (lR,3r,5S)-8-tert-butyl 3-methyl 8-azabicyclo[3.2.1"|octane-3,,8-dicarboxylate:
To a solution of commercially available (li?,3r,55)-8-(tert-butoxycarbonyl)-8- azabicyclo[3.2.1]octane-3-carboxylic acid (10.0 g, 39.2 mmol) and methanol (4.75 mL, 118 mmol) in methylene chloride (200 mL) was added EDC (11.3 g, 58.8 mmol), diisopropylethylamine (13.7 mL, 78 mmol) and DMAP (0.479 g, 3.92 mmol). The resulting solution was stirred at rt for 16 h. The reaction solution was washed with potassium bisulfate (1 N, 200 mL), water (200 mL), saturated sodium bicarbonate, dried over sodium sulfate, and concentrated to give the title compound. LC/MS: (M+l)+: 270.1.
References:
WO2014/18764,2014,A1 Location in patent:Page/Page column 59
1222996-05-5
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18107-18-1
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1548548-51-1
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