Ammonium Chloride → HCID 86733283, compound

HRID 1606341Notes

Reaction equation

HRID 1606341 reaction equation
[CH3:1][Li].[O:3]1[C@H:5]2[CH2:6][C@H:7]3[C@:22]([CH3:24])([CH2:23][C@@H:4]12)[C@@H:21]1[C@H:10]([C@H:11]2[C@:18]([CH3:26])([CH2:19][C:20]1=[O:25])[C@@H:14]([C:15](=[O:17])[CH3:16])[CH2:13][CH2:12]2)[CH2:9][CH2:8]3.[Cl-].[NH4+]>CCOCC>[OH:3][C@@H:5]1[C@@H:4]([CH3:1])[CH2:23][C@@:22]2([CH3:24])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[C:20](=[O:25])[CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86733130HCID 86733130, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 86733283HCID 86733283, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A 1.6 molar solution of methyl lithium in ether (30 ml.) was added to a stirred suspension of cuprous iodide (4.56 g.) in dry ether (100 ml.) under nitrogen at -20°. A cold solution of 2α,3α-epoxy-5α-pregnane-11,20-dione (1.33 g.) in dry ether (20 ml.) was then added and the mixture was maintained at 0° for 40 hours and then at room temperature for 4 hours. The mixture was then poured into aqueous ammonium chloride solution and extracted into ethyl acetate. The organic extract was washed with water, dried (MgSO4) and evaporated in vacuo. The residue (2.9 g.) was purified by preparative TLC and crystallisation from methyl acetate/petroleum ether to give the title compound (0.5 g.) m.p. 142°-146° [α]D + 121+ (c 0.8).

Workup

  1. temperaturethe mixture was maintained at 0° for 40 hours
  2. extractionextracted into ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue (2.9 g.) was purified by preparative TLC and crystallisation from methyl acetate/petroleum ether

Sources & evidence

ORD record
ord-12547c089dc34e96be6ebbed6c87cdb0
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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