Isoxazolidine → HCID 58562538, compound

HRID 1896868Notes

Reaction equation

HRID 1896868 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[O:12]1[CH2:16][CH2:15][CH2:14][NH:13]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([N:13]3[CH2:14][CH2:15][CH2:16][O:12]3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 136333IsoxazolidineHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 58562538HCID 58562538, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,4-dioxaspiro[4.5]decan-8-one (358.5 mg, 2.3 mmol), and isoxazolidine (168 mg, 2.3 mmol), and sodium triacetoxyborohydride (1.46 g, 6.9 mmol) were taken in acetonitrile and stirred for 18 h at room temperature. The mixture concentrated under vacuum and the residue basified with NaHCO3, saturated with solid NaCl and extracted with EtOAc/iPrOH (4:1) four times. Organic layer separated, dried over Na2SO4 and evaporated. Residue purified by silica column chromatography to give the title compound.

Workup

  1. concentrationThe mixture concentrated under vacuum
  2. extractionextracted with EtOAc/iPrOH (4:1) four times
  3. customOrganic layer separated
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customResidue purified by silica column chromatography

Sources & evidence

ORD record
ord-2a25b61fff9a41198026c5219bef5727
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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