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

HRID 1477188ノート

反応式

HRID 1477188 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 21584188Chloroform methanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2eb16ab579144b7280e4e3b2bfdeded0
出典データセット
uspto-grants-2016_08
特許番号
US09403767B2

反応ノート

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