HCID 68429245, compound → HCID 72330250, compound

HRID 2092022Notes

Reaction equation

HRID 2092022 reaction equation
[OH:1][CH2:2][CH:3]1[CH:8]([N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[CH2:7][CH:6]2[CH2:20][CH:4]1[C:5]2([CH3:22])[CH3:21].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[O:19]=[C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17](=[O:18])[N:9]1[CH:8]1[CH2:7][CH:6]2[CH2:20][CH:4]([C:5]2([CH3:21])[CH3:22])[CH:3]1[CH:2]=[O:1]

Participants

4

Reactant 2

HCID 68429245HCID 68429245, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 72330250HCID 72330250, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

rac-2-[2-(Hydroxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-yl]-1H-isoindole-1,3(2H)-dione (750 mg, 2.51 mmol), silica gel (0.75 g) and pyridinium chlorochromate (1.08 g, 5.01 mmol) were stirred in dichloromethane (20 mL) at room temperature for 2 hours. After completion of the reaction, the reaction solution was filtered through celite, and the filtrate was evaporated. The resulting residue was purified by column chromatography (hexane/ethyl acetate=5/1→3/1) to give the desired product (61% yield).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction solution was filtered through celite
  3. customthe filtrate was evaporated
  4. customThe resulting residue was purified by column chromatography (hexane/ethyl acetate=5/1→3/1)

Sources & evidence

ORD record
ord-33342cbcd8aa4ca9bdacf340c30cbaa0
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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