PRASAD PRAGATI KISHORE (IN)
REDDI RAMBABU (IN)
AMENDED CLAIMS received by the International Bureau on 23 August 2016 (23.08.2016) WE CLAIM: 1. A one step room temperature process for the selective synthesis of regio and diastereo 1,2-azidoalcohols from alkenes comprising a) adding iodine solution to a stirred solution of alkene substrate in a solvent system comprising N,N-dimethyl formamide (DMF) and dimethyl sulfoxide (DMSO) in ratio the 1 :] followed by addition of co-oxidant at 0°C to -5°C; b) adding base to reaction mixture of step (a) followed by addition of azide source at a temperature ranging between Q°C to -5°C; c) stirring the reaction mixture of step (b) at a temperature ranging between 25 to 30°C for 8-12 hours to afford 1,2-azidoalcohols. 2. The process as claimed in claim 1, wherein said azide source is sodium azide. 3. The process as claimed in claim 1 , wherein said base is selected from triethylamine (Et3N), potassium carbonate (K2CO3), potassium tert-butoxide (KtOBu), sodium hydride (NaH), l,8-Diazabicycloundec-7-ene (DBU). 4. The process as claimed in claim 1, wherein said co-oxidant is selected from anhydrous tert-butyl hydroperoxide (TBHP) or 30%-50% aq. H2O2 at the temperature ranging from 25°C to 35°C. 5. The process as claimed in claim 1, wherein yield of said process is in the range of 70- 95%. 6. The process as claimed in claim 1 , wherein said process is metal free. 7. Novel regio and diastereo 1,2-azidoalcohols are included 2-azido-l-(2- bromophenyl)ethan- 1 -ol, 1 -azido-2-phenylpropan-2-ol, 1 -azido-4-(benzyloxy)-2- methylbutan-2-ol, 3-azido-4-(benzyloxy)-2-methylbutan-2-ol, Syn-2-azido-l- phenylpropane- 1 ,3-diol, 2-azido- 1 -(4-methoxyphenyl)propane- 1 ,3-diol, 2-azido-2- phenylethan-1-ol, 2-azido-2-(p-tolyl)ethan-l-ol, 2-azido-2-(2-bromophenyl)ethan-l-ol, 2- azido-2-(3-nitrophenyl)ethan-l-ol, 2-azido-4-(benzyloxy)-2-methyIbutan-l-ol, 3-azido-l- (benzyloxy)-3-methylbutan-2-o], 3-azido-3-(4-methoxyphenyl)propane-l,2-diol. 8. A process for preparation of chloramphenicol from 1 ,2-azidoaacohol comprising the steps of: a) adding 20% palladium hydroxide on carbon to a stirred solution of azidoalcohol in methanol under ¾ atmosphere at a temperature ranging between 25°C to afford aminodiol; b) adding methyl dichloroacetate into aminodiol of step (a) and heating the solution at a temperature ranging around 90°C for 1 hour to afford crude product; c) Adding crude product of step (b) into nitrating mixture at a temperature ranging around -20°C; d) Stirrine the solution of step c at a temperature of 0°C for 1 hour to afford chloramphenicol. 9. The process as claimed in claim 8, wherein said 1,2-azidoalcohol is Syn-2-azido-l- phenylpropane-1 ,3-diol. 10. The process as claimed in claim 8, wherein said nitrating mixture of step (c) is mixture of nitric acid and sulphuric acid (cone. HNO3: cone. H2SO4 (1:1)). 11. A process for preparation of tert-butyl anti-2,3-dihydroxy-l-(4- methoxyphenyl)propyl)carbamate from 1,2-azidoalchohol comprising the steps of: a) adding 20% palladium hydroxide on carbon to a stirred solution of azidoalcohol in solvent under H2 atmosphere at a temperature ranging between 25°C for 12 hours to afford aminodiol; b) adding Boc anhydride ((Boc)2O) and triethyl amine (Et3N) to a stirred solution of step (a) in dicholoromethane and allowing stirring at a temperature ranging from 25°C for 2 hours to afford Tert-butyl anti-2,3-dihydroxy-l-(4- methoxyphenyl)propyl)carbamate . 12. The process as claimed in claim 11, wherein said 1,2-azidoalcohol is 3-azido-3-(4- methoxyphenyl)propane- 1 ,2-diol. 13. The process as claimed in claim 11, wherein said process further comprises adding sodium hydride to a solution of tert-butyl anti-2,3-dihydroxy-l-(4- methoxyphenyl)propyl)carbamate in THF under nitrogen atmosphere at a temperature ranging from 25°C to 30°C with constant stirring for the period ranging from 3 to 3.5 hours to afford (4R,5R)-5-(hydroxymethyl)-4-(4-methoxyphenyl) oxazolidin-2-one. |
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