Triethylamine → 17-Hydroxy-16-methylidenepregna-1,4,9(11)-triene-3,20-dione

HRID 1285316Notes

Reaction equation

HRID 1285316 reaction equation
C[O:2]P(OC)OC.C(N(CC)CC)C.C1(S([CH2:23][C:24]2[C@@H:25]([C@:29]3([CH3:46])[C@@H:42]([CH:43]=2)[C@H:41]2[C:32]([C@:33]4([CH3:45])[C:38]([CH2:39][CH2:40]2)=[CH:37][C:36](=[O:44])[CH:35]=[CH:34]4)=[CH:31][CH2:30]3)[C:26](=[O:28])[CH3:27])=O)C=CC=CC=1>C1(C)C=CC=CC=1.CO>[OH:2][C@:25]1([C@:29]2([CH3:46])[C@H:42]([C@H:41]3[C:32](=[CH:31][CH2:30]2)[C@:33]2([CH3:45])[C:38](=[CH:37][C:36](=[O:44])[CH:35]=[CH:34]2)[CH2:39][CH2:40]3)[CH2:43][C:24]1=[CH2:23])[C:26](=[O:28])[CH3:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8472Trimethyl phosphiteHCID 18601425HCID 18601425, compound

Product 1

HCID 308215017-Hydroxy-16-methylidenepregna-1,4,9(11)-triene-3,20-dione

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Trimethylphosphite (0.3 ml) and triethylamine (0.3 ml) are added to a solution of 16(phenylsulfinylmethyl)pregn-1,4,9(11),15-tetraene-3,20-dione (VIB, Example 18, 538 mg of the mixed isomers) in toluene (5 ml) and methanol (0.7 ml). The mixture was heated at 85° in a sealed vial until the reaction was complete. The reaction mixture was poured into a buffer solution and extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over sodium sulfate, and concentrated to a solid which is recrystallized from ethyl acetate to give the title compound. NMR (CDCl3) 0.70, 1.36, 2.26, 5.10, 5.51, 6.00, 6.20 and 7.17 δ.

Workup

  1. temperatureThe mixture was heated at 85° in a sealed vial until the reaction
  2. additionThe reaction mixture was poured into a buffer solution
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to a solid which
  8. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-541f6c4197304912a224ad5390c641f9
Source dataset
uspto-grants-1986_01
Patent number
US04567001

Reaction notes

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