3-Bromobenzyl bromide → HCID 86617853, compound

HRID 552886Notes

Reaction equation

HRID 552886 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:8][C@H:9]([C:11]([O:13][CH3:14])=[O:12])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Br:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH2:35]Br>CN(C=O)C>[Br:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH2:35][C@@:9]([CH3:10])([C:11]([O:13][CH3:14])=[O:12])[N:8]=[C:7]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 699793-Bromobenzyl bromideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 11119053HCID 11119053, compound

Product 1

HCID 86617853HCID 86617853, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of methyl N-(diphenylmethylene)alaninate (2.6 g, 9.7 mmol) in DMF (20 mL) cooled to 0° C. was added NaHMDS (12.2 mL, 12.2 mmol, 1M in THF) slowly via syringe and the reaction mixture was stirred at 0° C. for 15 min at which point 3-bromo-benzyl bromide (2.55 g, 10.2 mmol) in DMF (10 mL) was added slowly via syringe. The reaction mixture was allowed to warm to rt over 16 h, quenched with aq NH4Cl and water, extracted with EtOAc, washed with aq LiCl (×3), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography (120 g silica, 0-15% EtOAc in hexanes) to provide methyl 3-bromo-N-(diphenylmethylene)-α-methylphenylalaninate.

Workup

  1. additionwas added slowly via syringe
  2. customquenched with aq NH4Cl and water
  3. extractionextracted with EtOAc
  4. washwashed with aq LiCl (×3)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography (120 g silica, 0-15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e0fc41f1c9ec437c8555f19c7c91ffab
Source dataset
uspto-grants-2011_05
Patent number
US07951949B2

Reaction notes

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