Methyl 2-(bromomethyl)-4-methoxybenzoate → HCID 68509225, compound

HRID 1715159Notes

Reaction equation

HRID 1715159 reaction equation
CO[C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[CH2:12]Br.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>CO.C(N(CC)CC)C>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([N:28]2[CH2:12][C:5]3[C:4](=[CH:9][CH:8]=[C:7]([O:10][CH3:11])[CH:6]=3)[C:3]2=[O:14])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 2

HCID 139928Methyl 2-(bromomethyl)-4-methoxybenzoateHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 68509225HCID 68509225, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-bromomethyl-4-methoxy-benzoic acid methyl ester (1.28 g, 4.94 mmol, 1.0 equiv) in methanol (9 mL) and triethylamine (0.83 mL) was added 4-amino-piperidine-1-carboxylic acid tert-butyl ester (1.04 g, 5.19 mmol, 1.05 equiv; commercially available) and the reaction stirred at rt overnight. The reaction mixture was poured on crashed ice/diluted HCl, extracted with ethyl acetate, the combined organic phases washed with a sat. solution of NaHCO3 and water, dried over Na2SO4 and concentrated by evaporation under reduced pressure. The crude material was purified with silica column chromatography eluting with hexane/ethyl acetate (3:7) yielding 0.84 g (49%) of the title compound as white crystals. MS (ISP): 347.3 [M+H]+.

Workup

  1. additionThe reaction mixture was poured
  2. extractionextracted with ethyl acetate
  3. washthe combined organic phases washed with a sat. solution of NaHCO3 and water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe crude material was purified with silica column chromatography
  7. washeluting with hexane/ethyl acetate (3:7)

Sources & evidence

ORD record
ord-e8e8e6ba52ef4662ba78840775cd762b
Source dataset
uspto-grants-2010_09
Patent number
US07799806B2

Reaction notes

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