Triethylamine → HCID 86594553, compound

HRID 1744056Notes

Reaction equation

HRID 1744056 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[NH2:6].[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[O-]S([O-])(=O)=O.[Mg+2].C(N(CC)CC)C.[BH4-].[Na+]>C(Cl)Cl.CO>[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH:6][C@@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[C:4]([O:3][CH3:2])=[O:11])=[CH:15][CH:14]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 707414-BromobenzaldehydeHCID 2723695Leucine methyl ester hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 86594553HCID 86594553, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To L-leucine methyl ester hydrochloride (1.427 g, 7.855 mmol), 4-bromobenzaldehyde (1.451 g, 7.855 mmol), and MgSO4 (0.1 g/mmol, 1 g) in CH2Cl2 (20 mL) was added triethylamine (840 μL, 8.25 mmol) dropwise and the reaction mixture was stirred overnight. The heterogeneous solution was filtered over celite, the filter cake washed several times with CH2Cl2 and the filtrate was concentrated in vacuo. The residue was dissolved in a minimal amount of MeOH and NaBH4 (300 mg, 7.855 mmol) was added portionwise at 0° C. and the reaction mixture was stirred for 3.5 hours. The reaction was quenched with water and the product was extracted with EtOAc (2×), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (EtOAc/Hex, 2/8) to afford methyl (2S)-2-[(4-bromobenzyl)amino]-4-methylpentanoate.

Workup

  1. filtrationThe heterogeneous solution was filtered over celite
  2. washthe filter cake washed several times with CH2Cl2
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionwas added portionwise at 0° C.
  5. stirringthe reaction mixture was stirred for 3.5 hours
  6. customThe reaction was quenched with water
  7. extractionthe product was extracted with EtOAc (2×)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. custompurified by flash chromatography over silica gel (EtOAc/Hex, 2/8)

Sources & evidence

ORD record
ord-2e15c7ea1dd64abcae5abe36997b8bc3
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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