Acetic Acid → N-Benzyl-N-methyl-1,4-dioxaspiro[4.5]decan-8-amine

HRID 1193362ノート

反応式

HRID 1193362 の反応式
[CH3:1][NH:2][CH:3]1[CH2:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.O>[CH2:13]([N:2]([CH3:1])[CH:3]1[CH2:12][CH2:11][C:6]2([O:7][CH2:8][CH2:9][O:10]2)[CH2:5][CH2:4]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 16786570N-methyl-1,4-dioxaspiro(4.5)decan-8-amine

生成物 1

HCID 22009899N-Benzyl-N-methyl-1,4-dioxaspiro[4.5]decan-8-amine収率 49%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

N-Methyl-1,4-dioxaspiro[4.5]decan-8-amine (4.0 g, 23.39 mmol, 1.0 eq.) was dissolved in DCM (70 ml); benzaldehyde (2.83 g, 28.07 mmol, 1.2 eq.) and AcOH (0.2 ml) were added and the mixture was stirred for 30 minutes at RT. NaBH(OAc)3 (14.8 g, 70.17 mmol, 3.0 eq.) was added at 0° C. and the reaction mixture was stirred for a further 14 hours at RT. After monitoring by TLC, water (100 ml) was added to the reaction and the phases were separated. The aqueous phase was extracted with 10% MeOH in DCM (2×100 ml). The combined org. phases were washed in succession with water (100 ml) and sat. NaCl solution (100 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 4% MeOH in DCM). Yield: 49% (3.0 g, 11.49 mmol)

後処理

  1. stirringthe reaction mixture was stirred for a further 14 hours at RT
  2. additionwas added to the reaction
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with 10% MeOH in DCM (2×100 ml)
  5. washphases were washed in succession with water (100 ml) and sat. NaCl solution (100 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. custompurified by column chromatography (silica gel, 4% MeOH in DCM)

出典と根拠

ORDレコード
ord-91419fe31823425f9dc729f9472c8c1e
出典データセット
uspto-grants-2014_03
特許番号
US08680159B2

反応ノート

読み込み中…