Magnesium Bromide → HCID 118194622, compound

HRID 529292Notes

Reaction equation

HRID 529292 reaction equation
[CH:1]1([CH2:5][CH:6]=[N:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3][CH2:2]1.[Mg+2].[Br-].[Br-].C[Si](C)(C)[O:20][C:21]([O:29][CH2:30][CH3:31])=[C:22]([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25].C1CCCCC1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:8]([NH:7][CH:6]([CH2:5][CH:1]1[CH2:4][CH2:3][CH2:2]1)[C:22]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])[C:21]([O:29][CH2:30][CH3:31])=[O:20])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 82241Magnesium BromideHCID 12614350Trimethyl[(1,2,2-triethoxyethenyl)oxy]silaneHCID 21867204Cyclohexane ethylacetateHCID 118201132HCID 118201132, compound

Product 1

HCID 118194622HCID 118194622, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-(2-cyclobutylethylidene)-1-phenylmethanamine (1.00 g, 5.3 mmol) was dissolved in 23 mL toluene, MgBr2.0Et2 (2.07 g, 8.0 mmol) was added and the mixture was stirred at room temperature for 15 minutes. Trimethyl(1,2,2-triethoxyvinyloxy)silane (1.83 g, 7.4 mmol) was added, and the mixture was stirred at room temperature. After 3 hours, the reaction was quenched with water (30 mL) and acidified to pH=2 with hydrochloric acid. The organic phase was washed with sat. NaHCO3, dried over Na2SO4 and the solvent was removed under vacuum to yield the crude product. Column chromatography (silica, cyclohexane:ethyl acetate 10:1) yielded 1.1 g ethyl 3-(benzylamino)-4-cyclobutyl-2,2-diethoxybutanoate.

Workup

  1. addition0Et2 (2.07 g, 8.0 mmol) was added
  2. stirringthe mixture was stirred at room temperature
  3. waitAfter 3 hours
  4. customthe reaction was quenched with water (30 mL)
  5. washThe organic phase was washed with sat. NaHCO3
  6. dry with materialdried over Na2SO4
  7. customthe solvent was removed under vacuum
  8. customto yield the crude product

Sources & evidence

ORD record
ord-48ebae4860504e72a7cd92e8ed05a9c3
Source dataset
uspto-grants-2016_05
Patent number
US09346853B2

Reaction notes

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