Isopropanol → HCID 90388261, compound

HRID 2201748Notes

Reaction equation

HRID 2201748 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[OH:14][C@H:15]1[C@:19]2([CH3:33])[CH2:20][C@H:21]3[C@H:30]([CH2:31][C@H:18]2[CH2:17][CH2:16]1)[C@@H:29]1[C@@H:24]([CH2:25][C:26](=[O:32])[CH2:27][CH2:28]1)[CH2:23][CH2:22]3.CC(O)C>CC(C)=O>[CH3:33][C@:19]12[C:15](=[O:14])[CH2:16][CH2:17][C@@H:18]1[CH2:31][C@H:30]1[C@@H:21]([CH2:22][CH2:23][C@H:24]3[C@@H:29]1[CH2:28][CH2:27][C:26](=[O:32])[CH2:25]3)[CH2:20]2

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 90388303HCID 90388303, compoundHCID 131709961Jones' reagent

Product 1

HCID 90388261HCID 90388261, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones reagent was added to a solution of compound 53 (115 mg, 0.42 mmol) in acetone (20 mL) at 0° C. until a brown-yellowish color persisted. After 10 min, 2-propanol (1.0 mL) was added to consume excess oxidant and then brine (50 mL) was added. The product was extracted into EtOAc (50 mL×3), and the combined extracts were dried, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel eluted with 25% EtOAc in hexanes) to give compound 54 (110 mg 4aR:4aS ratio 2.5:1) as a white solid: 1H NMR (CDCl3) δ 0.84 (s, 3H); 13C NMR (CDCl3) 4aR diastereomer δ 220.3, 212.2, 47.8, 45.6, 42.6, 39.8, 39.0, 38.5, 38.2, 38.1, 36.3, 35.4, 30.7, 28.5, 28.4, 27.1, 23.9, 13.5.

Workup

  1. customto consume excess oxidant
  2. additionbrine (50 mL) was added
  3. extractionThe product was extracted into EtOAc (50 mL×3)
  4. customthe combined extracts were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (silica gel eluted with 25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a55a48ed83c14b4f9d9d09141b6da566
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

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