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

HRID 1193362Notes

Reaction equation

HRID 1193362 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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)

Workup

  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)

Sources & evidence

ORD record
ord-91419fe31823425f9dc729f9472c8c1e
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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