Synthesis of (3S,5S)-3,5-diaminopiperidin-2-one as a conformationally restricted surrogate of Dab-Gly dipeptide |
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| Institution: | 1. Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany;2. Leibniz-Institut für Katalyse an der Universität Rostock e. V., Albert-Einstein-Str. 29a, 18059 Rostock, Germany;3. Department of Pharmacy, COMSATS Institute of Information Technology, Abbottabad, Pakistan;4. Al-Farabi Kazakh National University, Al-Farabi ave. 71, 050040 Almaty, Kazakhstan;1. Department of Materials Science and Engineering, Institute of Space Technology, Islamabad 44000, Pakistan;2. Centre for Climate Research and Development (CCRD), Department of Meteorology, COMSATS Institute of Information Technology, Islamabad 44000, Pakistan;3. Department of Biological Sciences and Chemistry, University of Nizwa, P.O. Box 33, Postal Code 616, Nizwa, Oman;4. DARIS Center for Scientific Research and Technology Development, University of Nizwa, P.O. Box 33, Postal Code 616, Nizwa, Oman;5. Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan;1. Testing and Analysis Center, Hebei Normal University, Shijiazhuang 050024, PR China;2. College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050024, PR China;3. Material Science and Engineering School, Shijiazhuang Tiedao University, Shijiazhaung 050043, PR China;4. Department of Chemistry, Handan College, Handan 056005, PR China;1. Division of Organic Chemistry, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune 411 008, India;2. Academy of Scientific and Innovative Research (AcSIR), CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune 411 008, India;3. Centre for Material Characterization, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune 411 008, India |
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| Abstract: | An efficient and stereospecific synthesis of chiral 3,5-diaminopiperidin-2-one as a novel conformationally restricted surrogate of 2,4-diaminobutanoyl (Dab)-Gly dipeptide has been achieved. The key steps include (i) ruthenium tetroxide (RuO4) oxidation of N-Boc-2-azidomethylpyrrolidines with a catalytic amount of RuO2·xH2O in a two-phase system of aq NaIO4/AcOEt and (ii) intramolecular transamidation of the resulting 2-azidomethylpyrrolidin-2-ones with 10% Pd–C in MeOH/H2O (12/1, v/v) under an H2 atmosphere (3 atm). This methodology represents a powerful tool for the synthesis of Dab-Gly dipeptide surrogate. |
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