Triethylamine → Methyl 8-{[(5-bromo-2-methylphenyl)acetyl]amino}-1,4-dioxaspiro[4.5]decane-8-carboxylate

HRID 922128Notes

Reaction equation

HRID 922128 reaction equation
[NH2:1][C:2]1([C:12]([O:14][CH3:15])=[O:13])[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[Br:23][C:24]1[CH:25]=[CH:26][C:27]([CH3:34])=[C:28]([CH2:30][C:31](Cl)=[O:32])[CH:29]=1>ClCCl>[Br:23][C:24]1[CH:25]=[CH:26][C:27]([CH3:34])=[C:28]([CH2:30][C:31]([NH:1][C:2]2([C:12]([O:14][CH3:15])=[O:13])[CH2:3][CH2:4][C:5]3([O:9][CH2:8][CH2:7][O:6]3)[CH2:10][CH2:11]2)=[O:32])[CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12182743Methyl 8-amino-1,4-dioxaspiro[4.5]decane-8-carboxylateHCID 51063875(5-Bromo-2-methylphenyl)acetyl chloride

Product 1

HCID 67375909Methyl 8-{[(5-bromo-2-methylphenyl)acetyl]amino}-1,4-dioxaspiro[4.5]decane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

At room temperature, 5.47 g (25.41 mmol) of methyl 8-amino-1,4-dioxaspiro[4.5]decane-8-carboxylate [T. Satoh et al., Tetrahedron 63 (2007), 4806-4813], 3.86 g (38.12 mmol) of triethylamine and 155 mg (1.27 mmol) of N,N-dimethylaminopyridine were dissolved in 45 ml of dichloromethane. A solution of 6.29 g (25.41 mmol) of (5-bromo-2-methylphenyl)acetyl chloride (Example 3A) in 45 ml of dichloromethane was then added dropwise to the mixture. The resulting reaction mixture was stirred at room temperature overnight. For work-up, the mixture was diluted with dichloromethane and the organic phase was washed with aqueous saturated sodium bicarbonate solution. After drying over sodium sulphate, the mixture was concentrated by evaporation and the residue was purified by chromatography on silica gel (mobile phase: hexane/ethyl acetate gradient/1% triethylamine) Evaporation and drying gave 3.64 g (34% of theory) of the title compound which was used without further characterization in the next step.

Workup

  1. customThe resulting reaction mixture
  2. washthe organic phase was washed with aqueous saturated sodium bicarbonate solution
  3. dry with materialAfter drying over sodium sulphate
  4. concentrationthe mixture was concentrated by evaporation
  5. customthe residue was purified by chromatography on silica gel (mobile phase: hexane/ethyl acetate gradient/1% triethylamine) Evaporation
  6. customdrying

Sources & evidence

ORD record
ord-9fea5488ddf540c19d5aef1337df0d66
Source dataset
uspto-grants-2016_03
Patent number
US09278925B2

Reaction notes

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