Tetrahydrofuran → HCID 15692384, compound

HRID 2224045Notes

Reaction equation

HRID 2224045 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C:17]3[C@:8]([CH3:22])([C@H:9]4[C@@:13]([CH2:15][CH:16]=3)([CH3:14])[C@@H:12]([OH:21])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.C1COCC1>[Pd].CO>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@:8]([CH3:22])([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@@H:12]([OH:21])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 15907973HCID 15907973, compound

Product 1

HCID 15692384HCID 15692384, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

75 mg of 3-methoxy-8β-methyl-estra-1,3,5(10),9(11)-tetraen-17β-ol (7a) was dissolved in a solvent mixture that consists of 3.5 ml of THF and 1.5 ml of methanol and stirred with 75 mg of palladium (10%, on magnesium carbonate) for 3.75 hours at room temperature under hydrogen atmosphere. Then, the reaction solution was filtered on Celite, the filtrate was evaporated to the dry state in a rotary evaporator, and the thus obtained TLC-uniform, foamy product (74 mg, 98%) was used without further purification in the next stage.

Workup

  1. filtrationThen, the reaction solution was filtered on Celite
  2. customthe filtrate was evaporated to the dry state in a rotary evaporator
  3. customthe thus obtained TLC-uniform, foamy product (74 mg, 98%) was used without further purification in the next stage

Sources & evidence

ORD record
ord-1a9c78e45178455abb479ecc0afe0b19
Source dataset
uspto-grants-2008_05
Patent number
US07378404B2

Reaction notes

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