Acetic Acid → Dimethyl-(8-phenyl-1,4-dioxa-spiro[4.5]dec-8-ylmethyl)-amine

HRID 76928Notes

Reaction equation

HRID 76928 reaction equation
[C:1]1([C:7]2([CH2:17]N)[CH2:16][CH2:15][C:10]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[C:21](B)#[N:22].[Na].[C:25](O)(=O)C>C(#N)C.C(Cl)(Cl)Cl.CO>[CH3:25][N:22]([CH3:21])[CH2:17][C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 20596179(8-Phenyl-1,4-dioxaspiro[4.5]decan-8-YL)methanamineHCID 101953985CID 101953985

Product 1

HCID 45026964Dimethyl-(8-phenyl-1,4-dioxa-spiro[4.5]dec-8-ylmethyl)-amine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21584188Chloroform methanolSolvent

Procedure

The title compound of step 4 (5.40 g, 21.8 mmol) was dissolved in acetonitrile (150 mL), and a cloudy solution was formed. Aqueous 37% formalin solution (30.6 mL, 407 mmol) was added. The batch was stirred for 20 min at RT and then mixed with sodium cyanoboron hydride (5.76 g, 91.7 mmol). The reaction was followed by DC in chloroform/methanol (9:1). After 4 h the solution was adjusted to pH 7 with acetic acid and concentrated to low volume in a vacuum. The residue was taken up in chloroform, washed with NaHCO3 solution and the aqueous phase extracted with ether. The combined organic phases were dried over Na2SO4 and concentrated to low volume in a vacuum. The raw product was purified by flash chromatography with chloroform/methanol (50:1→20:1→9:1).

Workup

  1. customa cloudy solution was formed
  2. concentrationconcentrated to low volume in a vacuum
  3. washwashed with NaHCO3 solution
  4. extractionthe aqueous phase extracted with ether
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. concentrationconcentrated to low volume in a vacuum
  7. customThe raw product was purified by flash chromatography with chloroform/methanol (50:1→20:1→9:1)

Sources & evidence

ORD record
ord-38dba17e245c462a92a6885cd31a8b7a
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

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