2H-1,2-Oxazine, tetrahydro- → HCID 58562695, compound

HRID 1896866Notes

Reaction equation

HRID 1896866 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[CH2:17][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][CH2:17][O:12]3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1421022H-1,2-Oxazine, tetrahydro-HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 58562695HCID 58562695, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,4-dioxaspiro[4.5]decan-8-one (358.5 mg, 2.3 mmol), and 1,2-oxazinane (200 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-f68850358f1743fe8a533d9a3ca89c8e
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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