Dimethylamine → HCID 28599418, compound

HRID 2263572Notes

Reaction equation

HRID 2263572 reaction equation
[CH3:1][N:2]([CH:4]=O)[CH3:3].[CH3:6]NC.CN(C(ON1N=[N:24][C:19]2[CH:20]=[CH:21][CH:22]=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([O-])(O)=O.[Na+]>C1COCC1.O>[CH3:1][N:2]([CH3:3])[CH2:4][C@H:19]([NH2:24])[CH2:20][CH:21]([CH3:6])[CH3:22]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 28599418HCID 28599418, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-Boc-D-Leu-OH (1 g, 4.1 mmol), DMF (5 mL), and dimethylamine (4.3 mL of a 2M solution in THF, 8.6 mmol) was treated with HBTU (2 g, 5.2 mmol) and stirred at ambient temperature overnight. The reaction mixture was added to saturated NaHCO3 (25 mL) and water (25 mL). The layers were separated and the aqueous layer was extracted with Et2O (3×40 mL). The combined organic extracts along with the white insoluble material, were stripped of solvent and treated with TFA (10 mL) during 3 h, at which point the TFA was evaporated in vacuo. The residue was coevaporated with toluene, dissolved in THF (50 mL), treated with LiAIH4 (1.6 g, 42 mmol), and the suspension held at reflux overnight. The reaction mixture was cooled in an ice bath and treated successively with IPA (10 mL) and 6M NaOH (5 mL); after stirring for 2 h, the suspension was filtered, concentrated in vacuo. The residue was suspended in brine (50 mL) and extracted with CH2Cl2 (3×15 mL). The combined organic extracts were dried (MgSO4), filtered and concentration in vacuo to afford an oil of (2R)-1-dimethylamino-2-amino-4-methyl-pentane which was used without further purification.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with Et2O (3×40 mL)
  3. additiontreated with TFA (10 mL) during 3 h, at which point the TFA
  4. customwas evaporated in vacuo
  5. dissolutiondissolved in THF (50 mL)
  6. additiontreated with LiAIH4 (1.6 g, 42 mmol)
  7. temperatureat reflux overnight
  8. temperatureThe reaction mixture was cooled in an ice bath
  9. additiontreated successively with IPA (10 mL) and 6M NaOH (5 mL)
  10. stirringafter stirring for 2 h
  11. filtrationthe suspension was filtered
  12. concentrationconcentrated in vacuo
  13. extractionextracted with CH2Cl2 (3×15 mL)
  14. dry with materialThe combined organic extracts were dried (MgSO4)
  15. filtrationfiltered
  16. concentrationconcentration in vacuo

Sources & evidence

ORD record
ord-3a155fc4f5ed4dc2bb9f598aa34d6ef9
Source dataset
uspto-grants-2010_12
Patent number
US07851637B2

Reaction notes

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