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Novel Approaches to the Synthesis of Carfentanil.

ADA267058

Publication Date	1993
Personal Author	Fraser-Reid, B. O.; Taba, K.; Banks, H. D.
Page Count	24
Abstract	Three novel approaches to the synthesis of carfentanil were investigated that did not involve the hydrolysis of the corresponding a-aminonitrile. Starting with commercially available 1-benzyl-4-piperidone, regioselective cleavage of an a,B-exoxysulfone, an aza (3.3) sigmatropic rearrangement and aminolysis of a 1-bromo-1,2-diene were studied. Of these, the most promising was the sigmatropic rearrangement.... Carfentanil, Aza sigmatropic rearrangement, Piperidine.
Keywords	Synthesis(Chemistry) Analgesics Cleavage Dienes Hydrolysis Piperidines Pharmacology Morphine Synthesis Carfentanil
Source Agency	Non Paid ADAS
NTIS Subject Category	57Q - Pharmacology & Pharmacological Chemistry 99D - Basic & Synthetic Chemistry
Corporate Authors	Edgewood Research, Development and Engineering Center, Aberdeen Proving Ground, MD.
Supplemental Notes	Prepared in collaboration with Duke Univ., Durham, NC. Dept. of Chemistry.
Document Type	Technical Report
Title Note	Final rept. May 91-May 92.
NTIS Issue Number	199321

Novel Approaches to the Synthesis of Carfentanil.

Novel Approaches to the Synthesis of Carfentanil.
ADA267058

Publication Date	1993
Personal Author	Fraser-Reid, B. O.; Taba, K.; Banks, H. D.
Page Count	24
Abstract	Three novel approaches to the synthesis of carfentanil were investigated that did not involve the hydrolysis of the corresponding a-aminonitrile. Starting with commercially available 1-benzyl-4-piperidone, regioselective cleavage of an a,B-exoxysulfone, an aza (3.3) sigmatropic rearrangement and aminolysis of a 1-bromo-1,2-diene were studied. Of these, the most promising was the sigmatropic rearrangement.... Carfentanil, Aza sigmatropic rearrangement, Piperidine.
Keywords	Synthesis(Chemistry) Analgesics Cleavage Dienes Hydrolysis Piperidines Pharmacology Morphine Synthesis Carfentanil
Source Agency	Non Paid ADAS
NTIS Subject Category	57Q - Pharmacology & Pharmacological Chemistry 99D - Basic & Synthetic Chemistry
Corporate Authors	Edgewood Research, Development and Engineering Center, Aberdeen Proving Ground, MD.
Supplemental Notes	Prepared in collaboration with Duke Univ., Durham, NC. Dept. of Chemistry.
Document Type	Technical Report
Title Note	Final rept. May 91-May 92.
NTIS Issue Number	199321