Isopropanol → HCID 58279940, compound

HRID 1958268Notes

Reaction equation

HRID 1958268 reaction equation
[OH:1][CH:2]1[CH2:10][CH:9]2[CH2:11][CH:3]1[CH:4]1[CH:8]2[C:7](=[O:12])[NH:6][C:5]1=[O:13].CC(O)C>S(=O)(=O)(O)O.O.CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[C:7]1(=[O:12])[CH:8]2[CH:4]([CH:3]3[CH2:11][CH:9]2[CH2:10][C:2]3=[O:1])[C:5](=[O:13])[NH:6]1

Participants

7

Reactant 2

HCID 3776IsopropanolHCID 58279952HCID 58279952, compound

Product 1

HCID 58279940HCID 58279940, compoundYield 96.1%

Reagents, catalysts & solvents 4

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

Chromium trioxide (2.7 g) was dissolved in concentrated sulfuric acid (2.3 mL) and water (10 mL). 12.17 mL of this solution was added dropwise to a 0° C. solution of rac-(3aS,4R,5S,7R,7aR)-5-hydroxyhexahydro-1H-4,7-methanoisoindole-1,3-dione (4.21 g) (prepared by modification of the procedures in Japanese Patent Publication JP 8-333368, Dec. 17, 1996) in 20 mL of acetone. After 1 hr, 2-propanol (20 mL) was added, and the reaction was stirred 30 min (orange color dissipates). The reaction was filtered through celite and concentrated in vacuo. Silica gel chromatography eluting with 98:2 CH2Cl2:MeOH afforded 4 g of the titled compound as a white solid.

Workup

  1. customprepared by modification of the procedures in Japanese Patent Publication JP 8-333368, Dec
  2. filtrationThe reaction was filtered through celite and
  3. concentrationconcentrated in vacuo
  4. washSilica gel chromatography eluting with 98:2 CH2Cl2

Sources & evidence

ORD record
ord-a8a77154364a46918bdb779bc034774b
Source dataset
uspto-grants-2013_04
Patent number
US08410111B2

Reaction notes

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