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

HRID 1193362노트

반응식

HRID 1193362 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-91419fe31823425f9dc729f9472c8c1e
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680159B2

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