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US 9,657,030 B2Granted
Transition metal-catalyzed processes for the preparation of N-allyl compounds and use thereof
AssigneeRhodes Technologies
InventorsJoshua Robert Giguere, Keith Edward McCarthy, Helge Alfred Reisch, Sergio Sandoval, Jake Larry Stymiest
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Abstract
The present disclosure provides processes for the N-dealkylation of tertiary amines and the use of transition metal catalysts to prepare tertiary N-allyl amine derivatives and secondary amine derivatives thereof. The tertiary amines can be alkaloids and, more particularly, the tertiary amines can be opioids. In specific embodiments, the present disclosure provides methods for use in processes for the synthesis of naloxone and naltrexone from oripavine.
Claims27
A method for making a compound of Formula (54)
- comprising
- contacting a compound of Formula (55)
- with a compound of Formula (56)
- in a solvent containing an additional base and a transition metal catalyst to provide the compound of Formula (54);
- wherein:
- R14 is selected from —OH and —OR17;
- R16 is selected from —OH, —H, and —OR17;
- the 6,7 bond, the 7,8 bond, and the 8,14 bond are each independently a single bond or a double bond, with the provisos that (1) if the 6,7 bond is a double bond, then the 7,8 bond is a single bond, (2) if the 7,8 bond is a double bond, then the 6,7 and 8,14 bonds are each a single bond, and (3) if the 8,14 bond is a double bond, then the 7,8 bond is a single bond and R16 is not present;
- R15 is selected from —OH, —H, —OR17, ═O, and ═CH2 with the proviso that if the 6,7 bond is a double bond, then R15 is selected from —OH, —H, and —OR17;
- R22 is —OC(O)X;
- X is selected from —Cl, —Br, and —I;
- and
- R17 is an oxygen protecting group.
10 more elements
Dependencies are inferred from the claim text.