2-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 3-(aMinocarbonyl)-, 1,1-diMethylethyl ester, (1S,3R,5S)- synthesis
- Product Name:2-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 3-(aMinocarbonyl)-, 1,1-diMethylethyl ester, (1S,3R,5S)-
- CAS Number:1564266-79-0
- Molecular formula:C11H18N2O3
- Molecular Weight:226.27
![2-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid, 2-(1,1-dimethylethyl) ester, compd. with N-ethyl-N-(1-methylethyl)-2-propanamine (1:1), (1S,3R,5S)-](/CAS/20211123/GIF/1564266-83-6.gif)
1564266-83-6
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1564266-79-0
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Yield:1564266-79-0 58%
Reaction Conditions:
Stage #1: N-Boc-D-trans-4,5-methanoproline diisopropylethylamine saltwith methanesulfonyl chloride;N-ethyl-N,N-diisopropylamine in tetrahydrofuran; for 1 h;
Stage #2: with ammonia in tetrahydrofuran; for 1 h;
Steps:
1.28
General procedure: To the solution of 17a (4.88 g, 13.7 mmol) dissolved in dry THF (40 mL), DIPEA (2.39 mL, 1 equiv) and mesyl chloride (1.57 mL, 1.5 equiv) was added slowly.
The resulting suspension was stirred for 1 h, followed by saturation with ammonia.
After saturation, the reaction mixture was stirred for 1 h.
Following stirring, the reaction mixture was filtered to remove the solid.
The filtrate was concentrated under vacuum and purified by flash chromatography to give pure product 14c.
References:
Dong, Jizhe;Gong, Yanchun;Liu, Jun;Chen, Xiangfeng;Wen, Xiaoan;Sun, Hongbin [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 4,p. 1383 - 1393]
24424-99-5
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1564266-79-0
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932040-48-7
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1091626-35-5
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![(1S,3R,5S)-2-tert-Butyl 3-ethyl 2-azabicyclo[3.1.0]hexane-2,3-dicarboxylate](/CAS/20180702/GIF/871727-40-1.gif)
871727-40-1
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1564266-79-0
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