Trifluoroacetic anhydride → HCID 14537017, compound

HRID 1655648Notes

Reaction equation

HRID 1655648 reaction equation
[C:1]([C@H:3]1[C@H:8]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:6]2([CH3:7])[C:5](=[O:25])[CH2:4]1)[C@:17]1([CH3:18])[C@H:12]([CH2:13][C:14](=[O:24])[CH2:15][C@:16]1(O)[CH3:22])[CH2:11][CH2:10]3)#[N:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(O)(=O)C.C(OCC)(=O)C>[C:1]([C@H:3]1[C@H:8]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:6]2([CH3:7])[C:5](=[O:25])[CH2:4]1)[C@:17]1([CH3:18])[C@H:12]([CH2:13][C:14](=[O:24])[CH:15]=[C:16]1[CH3:22])[CH2:11][CH2:10]3)#[N:2]

Participants

5

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 14537015HCID 14537015, compound

Product 1

HCID 14537017HCID 14537017, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.0 g of 15β-cyano-1β-hydroxy-1α-methyl-5α-androstane-3,17-dione is stirred in 20 ml of glacial acetic acid with 6 ml of trifluoroacetic anhydride at room temperature. After 4 hours the solution is added to ice/water. The precipitated product is suctioned off, dissolved in ethyl acetate and washed with water. 1.7 g of 15β-cyano-1-methyl-5α-androst-1-ene-3,17-dione with a melting point of 193° C. is obtained.

Workup

  1. washwashed with water

Sources & evidence

ORD record
ord-2147678af6184bfd8913940bf5bfb285
Source dataset
uspto-grants-1993_10
Patent number
US05250712

Reaction notes

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