Pyridine → HCID 10339998, compound

HRID 850828Notes

Reaction equation

HRID 850828 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:20][C@@:18]2([CH3:19])[C@@H:14]([CH2:15][CH2:16][C:17]2=[O:21])[C@H:13]2[C@H:4]1[C:5]1[CH:6]=[CH:7][C:8]([OH:22])=[CH:9][C:10]=1[CH2:11][CH2:12]2.C1(C)C=CC(S(O)(=O)=[O:30])=CC=1.N1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1(C)C=CC=CC=1.O1CCCC1.O1C=CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C@H:3]1[CH2:20][C@@:18]2([CH3:19])[C@@H:14]([CH2:15][CH2:16][C:17]2=[O:21])[C@H:13]2[C@H:4]1[C:5]1[CH:6]=[CH:7][C:8]([O:22][CH:39]3[CH2:38][CH2:37][CH2:36][CH2:35][O:30]3)=[CH:9][C:10]=1[CH2:11][CH2:12]2

Participants

8

Reactant 3

HCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 1120881311beta-Methoxy-3-hydroxy-estra-1,3,5(10)-trien-17-one

Product 1

HCID 10339998HCID 10339998, compound

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 80803,4-dihydro-2H-pyranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2.0 g of 11β-methoxy-3-hydroxy-estra -1,3,5(10)-trien-17-one in 20 ml of toluene, 5 ml of tetrahydrofuran and 3.0 ml of dihydropyran is stirred with 20 mg of para-toluenesulfonic acid for 24 hours at room temperature. Then, 0.5 ml of pyridine is added, diluted with ethyl acetate, washed with sodium bicarbonate solution as well as with saturated sodium chloride solution, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/acetone. 1.9 g of 11β-methoxy-3-tetrahydropyranyloxy-estra -1,3,5(10)-trien-17-one is obtained as crystals with a melting point of 147° C., [α]D22 =+147.2° (c=0.5% in pyridine).

Workup

  1. washwashed with sodium bicarbonate solution as well as with saturated sodium chloride solution
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customchromatographed on silica gel with hexane/acetone

Sources & evidence

ORD record
ord-d42a695279444eb592a0df2f429b74fc
Source dataset
uspto-grants-2000_01
Patent number
US06018062

Reaction notes

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