Butanoic acid, 2,2-dimethyl-3-[(phenylmethyl)amino]-, methyl ester → Methyl 3-amino-2,2-dimethylbutanoate

To a solution of methyl 3-(benzylamino)-2,2-dimethylbutanoate (5 g) in MeOH (150 ml) was added 10% palladium on carbon (1.5 g) at rt and the reaction mixture was stirred under hydrogen (balloon pressure) overnight at rt. After completion, the reaction mixture was filtered over a celite pad and the residue was washed with MeOH (25 ml). A saturated solution of hydrogen chloride in MeOH (50 ml) was added to the reaction mixture and allowed to stir overnight at rt. Methanol was removed under reduced pressure and the crude mass was triturated with diethyl ether (50 ml) to give the hydrochloride salt of the title compound (2.6 g). 1H NMR (400 MHz, DMSO-d6): δ 1.11-1.15 (m, 9H), 3.41-3.43 (m, 1H), 3.64 (s, 3H), 8.148 (bs, 3H).

1. filtrationAfter completion, the reaction mixture was filtered over a celite pad
2. washthe residue was washed with MeOH (25 ml)
3. additionA saturated solution of hydrogen chloride in MeOH (50 ml) was added to the reaction mixture
4. stirringto stir overnight at rt
5. customMethanol was removed under reduced pressure
6. customthe crude mass was triturated with diethyl ether (50 ml)

ORD record

ord-381bcc018d004e79bd3652efa3e1745e

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221826B2