Water → HCID 67712534, compound

HRID 233663Notes

Reaction equation

HRID 233663 reaction equation
C(O[C:4]([N:6]1[CH2:17][CH2:16][C:9]2([O:13][CH2:12][C:11](=[N:14]O)[CH2:10]2)[CH2:8][CH2:7]1)=O)C.COCCO[AlH2-]O[CH2:25][CH2:26][O:27]C.[Na+].[OH2:30].C1C[O:34]CC1>>[C:9]([OH:34])(=[O:13])/[CH:16]=[CH:25]\[C:26]([OH:27])=[O:30].[NH2:14][CH:11]1[CH2:10][C:9]2([CH2:8][CH2:7][N:6]([CH3:4])[CH2:17][CH2:16]2)[O:13][CH2:12]1

Participants

5

Reactant 4

HCID 962Water2×HCID 8028Tetrahydrofuran3×HCID 16684438Red-Al3×HCID 74043784HCID 74043784, compound

Product 1

HCID 67712534HCID 67712534, compound

Procedure

8-Ethoxycarbonyl-1-oxa-8-azaspiro[4.5]decan-3-one oxime (15.2 g, 0.063 mol) was dissolved in dry THF (400 ml) and added dropwise to a stirred solution of Vitride (71 ml, 0.25 mol) in THF (400 ml) cooled with an ice bath. After stirring the reaction overnight at room temperature additonal Vitride (35 ml) in THF (200 ml) was added and stirring was continued for 24 hours. Decomposition of the complex and excess Vitride with successive addition of water, 15% NaOHaq and water was carried out. The THF was filtered and evaporated to give the crude amine which was purified by chromatography on silica gel and elution with ammoniated 2-20% MeOH/CHCl3. The crude amine was dissolved in ethyl acetate and maleic acid was added. The precipitated salt was recrystallized from isopropanol/ethyl acetate to give the title product.

Workup

  1. temperaturecooled with an ice bath
  2. additionwas added
  3. stirringstirring
  4. filtrationThe THF was filtered
  5. customevaporated
  6. customto give the crude amine which
  7. customwas purified by chromatography on silica gel and elution with ammoniated 2-20% MeOH/CHCl3
  8. dissolutionThe crude amine was dissolved in ethyl acetate
  9. additionmaleic acid was added
  10. customThe precipitated salt was recrystallized from isopropanol/ethyl acetate

Sources & evidence

ORD record
ord-3d46c85080b74b1e821f63bda7b11b56
Source dataset
uspto-grants-1997_01
Patent number
US05594000

Reaction notes

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