Benzenemethanamine, 3-bromo-N-methyl- → 1-Benzyl-4-[(3-bromo-benzyl)-methyl-amino]-pyrrolidine-2-carboxylic acid

HRID 490656

Reaction equation

HRID 490656 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][C:8](=O)[CH2:7][N:6]1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4].[Br:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[CH2:22][NH:23][CH3:24].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl.CC(O)=O>[CH2:11]([N:6]1[CH2:7][CH:8]([N:23]([CH2:22][C:21]2[CH:25]=[CH:26][CH:27]=[C:19]([Br:18])[CH:20]=2)[CH3:24])[CH2:9][CH:5]1[C:3]([OH:2])=[O:4])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 457588Benzenemethanamine, 3-bromo-N-methyl-HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 67548133Benzyl-4-oxo-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 675479001-Benzyl-4-[(3-bromo-benzyl)-methyl-amino]-pyrrolidine-2-carboxylic acidYield 65%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzyl-4-oxo-pyrrolidine-2-carboxylic acid methyl ester (1 mmol), (3-bromo-benzyl)-methyl-amine (1 mmol) in 2 mL of CH2Cl2 were added NaBH(OAc)3 (2 mmol) and 5 drops of AcOH, and the resulting mixture was stirred for 3 h. The mixture was treated with aq. NaHCO3, extracted by CH2Cl2 (3×5 mL), and the combined extracts were washed by brine (10 mL), dried over Na2SO4, and concentrated to give 261.3 mg of crude product in 65% yield.

Workup

  1. extractionextracted by CH2Cl2 (3×5 mL)
  2. washthe combined extracts were washed by brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-832e4fc1a3a248cd9909c7508557bc3f
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Linked notes

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