Dimethylamine → HCID 11423221, compound

A solution of (S)-Boc-Val-OH (1 g, 4.1 mmol), DMF (5 mL), and dimethylamine (4.3 ml of a 2 M solution in THF, 8.6 mmol) was treated with HBTU (2 g, 5.3 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 μL). 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, 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 a yellow oil of (2S)-1-dimethylamino-2-amino-3-methyl-butane which was used without further purification.

1. customThe layers were separated
2. extractionthe aqueous layer was extracted with Et2O (3×40 μL)
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. temperatureat reflux overnight
7. temperatureThe reaction mixture was cooled in an ice bath
8. stirringafter stirring for 2 h
9. filtrationthe suspension was filtered
10. concentrationconcentrated in vacuo
11. extractionextracted with CH2Cl2 (3×15 mL)
12. dry with materialThe combined organic extracts were dried (MgSO4)
13. filtrationfiltered
14. concentrationconcentration in vacuo

ORD record

ord-4cfc84ffbb5d4cf2a1cd28a06ae51d3f

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07851637B2