Acetone → HCID 69245759, compound

HRID 1593660Notes

Reaction equation

HRID 1593660 reaction equation
[CH2:1]([O:8][N:9]1[C:12]2([CH:17]=CC(=O)[CH:14](O)[CH:13]2[OH:20])[CH2:11][C:10]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][O:23]C(OC)(C)C.[CH3:29]C1C=CC(S(O)(=O)=O)=CC=1.[CH3:40][C:41]([CH3:43])=[O:42]>>[CH2:1]([O:8][N:9]1[C:12]23[CH:17]=[CH:43][C:41](=[O:42])[CH:40]([CH3:29])[C:13]2([O:20][CH2:22][O:23][CH:11]3[C:10]1=[O:21])[CH3:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 69177826HCID 69177826, compound

Product 1

HCID 69245759HCID 69245759, compoundYield 42%

Procedure

To a stirred solution of rac-(4R,5S,6S)-1-benzyloxy-5,6-dihydroxy-1-azaspiro[3.5]nona-8-ene-2,7-dione (2) (109 mg, 0.377 mmol) and 2,2-dimethoxypropane (0.24 ml, 1.885 mmol) in dry acetone (0.75 ml) was added at room temperature catalytic amount of p-TsOH (1% mmol). The resulting mixture was stirred at room temperature for 18 h, then quenched with saturated aqueous Na2CO3 solution (1 ml) and extracted with AcOEt (3×2 ml). The combined organic extracts were washed with brine (3 ml), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-AcOEt, 5:2) to give rac-(4R,5S,6S)-1-benzyloxy-5,6-dimethylmethylendioxy-1-azaspiro[3.5]nona-8-ene-2,7-dione (13) as a solid (52 mg, 42%).

Workup

  1. customquenched with saturated aqueous Na2CO3 solution (1 ml)
  2. extractionextracted with AcOEt (3×2 ml)
  3. washThe combined organic extracts were washed with brine (3 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane-AcOEt, 5:2)

Sources & evidence

ORD record
ord-842ff01be30b41b2999355d80e1e87e3
Source dataset
uspto-grants-2007_11
Patent number
US07297788B2

Reaction notes

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