Tetrahydrofuran → HCID 86754249, compound

HRID 1837114Notes

Reaction equation

HRID 1837114 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C@@H:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][CH2:3]2.[Li][CH3:22].[CH2:23]1C[O:26][CH2:25][CH2:24]1>C(Cl)Cl>[OH:20][C@:12]1([CH3:22])[CH2:13][CH2:14][C@@:15]2([CH3:16])[C@@H:10]([CH2:9][CH2:8][C@@H:7]3[C@@H:17]2[CH2:18][CH2:19][C@@:2]2([CH3:1])[C@H:6]3[CH2:5][CH2:4][C@@H:3]2[O:26][CH2:25][C:24]#[CH:23])[CH2:11]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 102028Androstan-3-oneHCID 178418348HCID 178418348, compound

Product 1

HCID 86754249HCID 86754249, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of 17β-propynyloxy)-5α-androstan-3-one (230 mg, 0.7 mmol) in dry THF (20 mL) was treated with MeLi (5 mL, 1M in THF, 5 mmol) at −70° C. After stirring the mixture at −70° C. for 0.5 hr, the cooling bath was removed and it was warmed to 10° C. The mixture was then quenched with NH4Cl solution (5 mL). The solvents were removed and the residue was extracted with EtOAc. The organic layer was washed with water, and brine. After drying over anhyd. MgSO4 the solution was filtered and evaporated to yield the crude product. This crude product was then dissolved in a small amount of CH2Cl2 and poured on a column of silica gel. Elution with toluene:acetone mixture (98:2) gave 3α-hydroxy-3β-methyl-17β-(2-propynyloxy)-5α-androstane (40 mg); TLC Rf (toluene:acetone 95:5)=0.31; and then 3β-hydroxy-3α-methyl-17β-(2-propynyloxy)-5α-androstane (70 mg) as a colorless solid; TLC Rf (hexane:acetone 7:3)=0.27.

Workup

  1. customthe cooling bath was removed
  2. temperatureit was warmed to 10° C
  3. customThe mixture was then quenched with NH4Cl solution (5 mL)
  4. customThe solvents were removed
  5. extractionthe residue was extracted with EtOAc
  6. washThe organic layer was washed with water, and brine
  7. customAfter drying over anhyd
  8. filtrationMgSO4 the solution was filtered
  9. customevaporated
  10. customto yield the crude product
  11. additionpoured on a column of silica gel
  12. washElution with toluene

Sources & evidence

ORD record
ord-ab82ebc366fd4115b74f98aeb78cfabb
Source dataset
uspto-grants-2004_08
Patent number
US06780853B1

Reaction notes

Loading…