Acetic Acid → HCID 57635030, compound

To a solution of 2.3 g (0.016 mole) of 2-methyl-3-oxobutanoic acid ethyl ester in 50 mL of dichloroethane was added 1.00 g (0.016 mole) of cyclopropylamine. The mixture was stirred for 1.5 hours and then 5.1 g (0.023 mole) of sodium triacetoxyborohydride and 0.96 g (0.016 mole) of acetic acid were added. The mixture was stirred at room temperature for 24 hours and then quenched by the addition of 50 mL of saturated aqueous sodium bicarbonate. The mixture was stirred for 20 minutes. The organic layer was separated and the aqueous layer was extracted with twice with 30 mL of dichloromethane. The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated. Purification of the residue by silica gel chromatography, eluting with hexanes-ethyl acetate (30:70) gave 1.5 g of (rac)-3-cyclopropylamino-2-methyl-butanoic acid ethyl ester.

1. stirringThe mixture was stirred at room temperature for 24 hours
2. customquenched by the addition of 50 mL of saturated aqueous sodium bicarbonate
3. stirringThe mixture was stirred for 20 minutes
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted with twice with 30 mL of dichloromethane
6. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customPurification of the residue by silica gel chromatography
10. washeluting with hexanes-ethyl acetate (30:70)

ORD record

ord-790c1600c554442285661b0e4c0c9771

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517873B2