Pyridine → 1alpha-Methyl-17beta,19-di(trimethylsiloxy)-5alpha-androstan-3-one

HRID 1834967Notes

Reaction equation

HRID 1834967 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:19]([CH2:20][CH2:21][C@:3]12[CH3:4])[C@:16]1([CH2:17][OH:18])[C@H:11]([CH2:12][C:13](=[O:23])[CH2:14][C@@H:15]1[CH3:22])[CH2:10][CH2:9]3.[CH3:24][Si:25]([CH3:28])([CH3:27])Cl.N1C=CC=CC=1>C1C=CC=CC=1>[CH3:22][C@@H:15]1[C@@:16]2([CH2:17][O:18][Si:25]([CH3:28])([CH3:27])[CH3:24])[C@@H:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:19]2[CH2:20][CH2:21][C@@:3]2([CH3:4])[C@H:5]3[CH2:6][CH2:7][C@@H:2]2[O:1][Si:25]([CH3:28])([CH3:27])[CH3:24])[CH2:12][C:13](=[O:23])[CH2:14]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 7061509617beta,19-Dihydroxy-1alpha-methyl-5alpha-androstan-3-one

Product 1

HCID 228015331alpha-Methyl-17beta,19-di(trimethylsiloxy)-5alpha-androstan-3-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 17β,19-dihydroxy-1α-methyl-5α-androstan-3-one, trimethylchlorosilane and pyridine in benzene is heated to its reflux temperature for a period of about 14 hours. The reaction mixture is vacuum filtered, the organic layer is washed with water, dried over magnesium sulfate and concentrated in vacuum. Crystallization of the residue from hexane yields 1α-methyl-17β,19-di(trimethylsiloxy)-5α-androstan-3-one.

Workup

  1. temperatureis heated to its
  2. temperaturereflux temperature for a period of about 14 hours
  3. filtrationfiltered
  4. washthe organic layer is washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuum
  7. customCrystallization of the residue from hexane

Sources & evidence

ORD record
ord-c9260c3151d44116bb965af33edb6bef
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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