Pyridine → 3alpha-Trifluoroacetoxy-5alpha-pregnane-11,20-dione

HRID 1606470Notes

Reaction equation

HRID 1606470 reaction equation
F[C:2](F)(F)[C:3]([O:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8])=O.N1C=CC=CC=1.O[C@@H]1[CH2:40][CH2:39][C@@:38]2([CH3:41])[C@@H:23]([CH2:24][CH2:25][C@@H:26]3[C@@H:37]2[C:36](=[O:42])[CH2:35][C@@:34]2([CH3:43])[C@H:27]3[CH2:28][CH2:29][C@@H:30]2[C:31](=[O:33])[CH3:32])C1>C(Cl)Cl>[F:8][C:7]([F:10])([F:9])[C:6]([O:5][C@@H:3]1[CH2:40][CH2:39][C@@:38]2([CH3:41])[C@@H:23]([CH2:24][CH2:25][C@@H:26]3[C@@H:37]2[C:36](=[O:42])[CH2:35][C@@:34]2([CH3:43])[C@H:27]3[CH2:28][CH2:29][C@@H:30]2[C:31](=[O:33])[CH3:32])[CH2:2]1)=[O:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydride2×HCID 104845Alphaxalone

Product 1

HCID 867333213alpha-Trifluoroacetoxy-5alpha-pregnane-11,20-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of trifluoroacetic anhydride (0.34 ml.) and pyridine (0.24 ml.) in methylene dichloride (10 ml.) was added to a cooled (-80°) and stirred solution of 3α-hydroxy-5α-pregnane-11,20-dione (0.50 g.) in methylene dichloride (20 ml.) and the mixture was allowed to warm up to room temperature. After 11/2 hours more trifluoroacetic anhydride (0.34 ml.) was added and the reaction was complete after 1/2 hour more. The solution was washed successively with water, sodium bicarbonate solution and water. The dried and concentrated solution afforded a crystalline residue that was triturated with petroleum to give the title compound as needles (0.44 g.) m.p. 107°-108°, [α]D + 96°.

Workup

  1. temperaturea cooled (-80°)
  2. washThe solution was washed successively with water, sodium bicarbonate solution and water
  3. customThe dried
  4. customconcentrated solution afforded a crystalline residue that
  5. customwas triturated with petroleum

Sources & evidence

ORD record
ord-d3ee28df45ca4559a4ecd285df8e95eb
Source dataset
uspto-grants-1976_04
Patent number
US03953429

Reaction notes

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