Trifluoroacetic acid → Trifluoroacetic anhydride
Reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4]>C(O)(=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([O:5][C:3](=[O:4])[C:2]([F:7])([F:6])[F:1])=[O:4]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Epoxidation of the 21-methoxy compound (7) with hexafluoroacetone trihydrate and 30% hydrogen peroxide produce a 2:1 mixture of 5α,10α- and 5β,10β-epoxides (8) as evidenced by NMR. As attempts to isolate pure 5α,10α-epoxide (8) were unsuccessful, the crude mixture was used directly on to the copper (I) catalyzed Grignard reaction, to obtain the 11β-[4-(N,N-dimethylamino)phenyl] derivative (9). Hydrolysis with trifluoroacetic acid restored the 4,9-diene-3,20-dione structure (10). Acetylation of the 17α-hydroxy compound (10) with the mixed anhydride formed from trifluoroacetic anhydride and acetic acid afforded the desired 19-norprogesterone compound (11).
Sources & evidence
- ORD record
- ord-ca5968a5d2c04dcab303d27b24d48b47
- Source dataset
- uspto-grants-2004_07
- Patent number
- US06768014B2
Reaction notes
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