Ozone → HCID 87173610, compound

HRID 2207859Notes

Reaction equation

HRID 2207859 reaction equation
C[C@@H]([C@@H:9]1[C@@:13]2([CH3:30])[CH2:14][CH2:15][C:16]3[C@@:21]4([CH3:29])[CH2:22][CH2:23][C:24]([C:26]([CH3:28])([CH3:27])[CH:20]4[CH2:19][CH2:18][C:17]=3[C@:12]2([CH3:31])[CH2:11][CH2:10]1)=[O:25])CCC=C(C)C.O=[O+][O-]>C(Cl)Cl>[CH3:28][C:26]1([CH3:27])[CH:20]2[C@@:21]([CH3:29])([C:16]3[CH2:15][CH2:14][C@@:13]4([CH3:30])[C@:12]([CH3:31])([C:17]=3[CH2:18][CH2:19]2)[CH2:11][CH2:10][C@@H:9]4[C@H:21]([CH3:20])[CH2:22][CH2:23][CH:24]=[O:25])[CH2:22][CH2:23][C:24]1=[O:25]

Participants

4

Reactant 2

HCID 24823OzoneHCID 3036241Lanosta-8,24-dien-3-one

Product 1

HCID 87173610HCID 87173610, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of lanosterone (4.27 g, 9.11 mmol) in CH2Cl2 (128 mL) was placed in a three-neck round bottom flask equipped with a magnetic stir bar, thermometer, a CaCl2 drying tube and a gas inlet tube. The mixture was stirred and cooled to −50° C., at which point ozone was passed through the mixture for 17 min. The reaction mixture was then purged with argon for 20 min and then concentrated in vacuo to ca. 5 mL. After diluting the crude material with CH2Cl2 (50 mL), the organic phase was then washed twice with water (50 mL) and dried with anhydrous MgSO4. The crude product was concentrated with a rotary evaporator and purified by silica gel chromatography (step gradient of 5:1 then 3:1 hexane/EtOAc) to afford 5 as a white solid (1.578 g, 3.958 mmol, 78% based on an initial purity of 56% for the commercial lanosterol). mp 110-115° C. IR (KBr) νmax 2722, 1725, 1709 cm−1. 1H NMR (CDCl3) δ 9.77 (t, J=1.9 Hz, 1H), 2.57 (ddd, J=7.1, 11.2, 15.7 Hz, 1H), 2.5-2.3 (m, 3H), 2.10-1.18 (m, 19H), 1.11 (s, 3H), 1.09 (s, 3H), 1.06 (s, 3H), 0.90 (d, J=6.3 Hz, 3H), 0.89 (s, 3H), 0.71 (s, 3H). 13C{1H} 6 (CDCl3) δ 217.8, 203.2, 135.2, 133.2, 51.2, 50.3, 49.9, 47.4, 44.5, 41.1, 36.9, 36.1, 36.0, 34.6, 30.90, 30.87, 28.2, 28.11, 26.33, 26.2, 24.3, 21.3, 21.1, 19.4, 18.7, 18.4, 15.9. HRMS calcd for C27H43O2 (M+H)+399.3258. found 399.3258.

Workup

  1. customequipped with a magnetic stir bar
  2. customThe reaction mixture was then purged with argon for 20 min
  3. concentrationconcentrated in vacuo to ca. 5 mL
  4. additionAfter diluting the crude material with CH2Cl2 (50 mL)
  5. washthe organic phase was then washed twice with water (50 mL)
  6. dry with materialdried with anhydrous MgSO4
  7. concentrationThe crude product was concentrated with a rotary evaporator
  8. custompurified by silica gel chromatography (step gradient of 5:1

Sources & evidence

ORD record
ord-a009df93b4ce4828822c80b90850d6ed
Source dataset
uspto-grants-2016_06
Patent number
US09376462B2

Reaction notes

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