Dimethylamine → (2R)-N1,N1,3-Trimethyl-1,2-butanediamine

A solution of Boc-D-Val-OH (940 mg), DMF (5 mL), and 2.0 M dimethylamine in THF (4.3 mL) was treated with HBTU (2.0 g) and stirred at ambient temperature overnight. The reaction mixture was added to saturated NaHCO3 (25 mL) and water (25 mL), then extracted 3×40 mL Et2O. The combined organics, 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 LiAlH4 (1.6 g), 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 2h, the suspension was filtered, concentrated, and brine (50 mL) added. Extraction with DCM (3×15 mL), drying of the combined organics on MgSO4, and concentration gave a foμL-smelling yellow oil of (2R)-1-dimethylamino-2-amino-3-methyl-butane which was used without further purification.

1. extractionextracted 3×40 mL Et2O
2. additiontreated with TFA (10 mL) during 3 h, at which point the TFA
3. customwas evaporated in vacuo
4. dissolutiondissolved in THF (50 mL)
5. additiontreated with LiAlH4 (1.6 g)
6. temperatureat reflux overnight
7. temperatureThe reaction mixture was cooled in an ice bath
8. additiontreated successively with IPA (10 mL) and 6M NaOH (5 mL)
9. stirringafter stirring for 2h
10. filtrationthe suspension was filtered
11. concentrationconcentrated
12. additionbrine (50 mL) added
13. extractionExtraction with DCM (3×15 mL)
14. customdrying of the
15. concentrationcombined organics on MgSO4, and concentration

ORD record

ord-405f457bf5d840abbeb2f90df3ab0175

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07851637B2