Diisopropylethylamine → HCID 18771980, compound

Temperature

80 °C

To a stirred solution of L-valine methyl ester hydrochloride (0.54 g, 3.24 mmol) in dry toluene (15 mL) at 80° C. was added DIEA (2.0 mL 11 mmol) followed by (6-bromo-2-pyridyl)formaldehyde (0.50 g, 2.70 mmol). The resulting mixture was heated at 80° C. for 3 h. The reaction was brought to RT and a solution of NaBH(OAc)3 (1.4 g, 6.75 mmol) in glacial AcOH (4 mL) was added. The resulting mixture was stirred for 15 h and concentrated by rotary evaporation. The resulting yellow oil was dissolved in CH2Cl2 (100 mL), washed with a saturated solution of NaHCO3 (aq) (50 mL), brine (50 mL), dried over Na2SO4, filtered, concentrated by rotary evaporation and purified by flash chromatography (2:1 hexanes/EtOAc) to afford the title compound as a pale-yellow oil. EI-MS m/z 301 (M+H).

1. customwas brought to RT
2. concentrationconcentrated by rotary evaporation
3. dissolutionThe resulting yellow oil was dissolved in CH2Cl2 (100 mL)
4. washwashed with a saturated solution of NaHCO3 (aq) (50 mL), brine (50 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated by rotary evaporation
8. custompurified by flash chromatography (2:1 hexanes/EtOAc)

ORD record

ord-04c53c17135440fba5536217cfc4e9a1

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07196104B2