Tetrahydrofuran → HCID 69904567, compound

HRID 1837118Notes

Reaction equation

HRID 1837118 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:18]([CH3:20])([CH2:19][C@@H:2]12)[C@@H:17]1[C@H:8]([C@H:9]2[C@@:13]([CH2:15][CH2:16]1)([CH3:14])[C:12](=[O:21])[CH2:11][CH2:10]2)[CH2:7][CH2:6]3.[CH3:22][CH:23]([CH3:25])[O-:24].[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[CH2:36]1COCC1>C(Cl)Cl>[OH:1][C@@H:3]1[C@@H:2]([O:24][CH:23]([CH3:25])[CH3:22])[CH2:19][C@@:18]2([CH3:20])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[O:21][CH3:36])[CH2:4]1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 3260420IsopropanolateHCID 6451240Aluminum(III) ChlorideHCID 13686727HCID 13686727, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 69904567HCID 69904567, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 3α-hydroxy-2β-isopropoxy-5α-androstan-17-one 17-dimethyl acetal (prepared by the epoxide opening of 2α,3α-epoxy-5α-androstan-17-one with isopropoxide, followed by ketalization of 17-one) (490 mg, 1.25 mmol) in dry THF (15 mL) was treated with LAH (48 mg, 1.33 mmol) and AlCl3 (332 mg, 2.5 mmol) at −30° C. After stirring the mixture at 23° C. for 1 hr, it was quenched with NH4Cl solution (2 mL). The solvents were removed and the residue was extracted with EtOAc. The organic layer was washed with dil. HCl, 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 hexane:acetone mixture (9:1) gave 3α-hydroxy-2β-isopropoxy-17β-methoxy-5α-androstane (43 mg) as a foam; TLC Rf (hexane:acetone 7:3)=0.41.

Workup

  1. customit was quenched with NH4Cl solution (2 mL)
  2. customThe solvents were removed
  3. extractionthe residue was extracted with EtOAc
  4. washThe organic layer was washed with dil. HCl, water, and brine
  5. customAfter drying over anhyd
  6. filtrationMgSO4 the solution was filtered
  7. customevaporated
  8. customto yield the crude product
  9. additionpoured on a column of silica gel
  10. washElution with hexane

Sources & evidence

ORD record
ord-e219f0550632453fa8368fe0ec202b9e
Source dataset
uspto-grants-2004_08
Patent number
US06780853B1

Reaction notes

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