Hydroxyamine hydrochloride → HCID 58374179, compound

Temperature

75 °C

To a mixture of (S)-ethyl 1-(1-(4-cyanophenyl)-2-methyl-1-oxopropan-2-yl)piperidine-3-carboxylate (90 mg, 0.274 mmol) in MeOH (5 mL) was added sodium borohydride (15 mg, 0.396 mmol). After 1 hr, the reaction was quenched with water. The reaction mixture was diluted with ethyl acetate and washed with sat NaCl. The organic layer was dried MgSO4, filtered, and concentrated. To a mixture of hydroxylamine hydrochloride (38.1 mg, 0.548 mmol) and sodium bicarbonate (92 mg, 1.096 mmol) in 2-propanol (10 mL) was added the crude product from step one. The reaction mixture was heated at 75° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with H2O. The organic layer was dried MgSO4, filtered, and concentrated to yield 100 mg of (3S)-ethyl 1-(1-hydroxy-1-(4-((Z)—N′-hydroxycarbamimidoyl)phenyl)-2-methylpropan-2-yl)piperidine-3-carboxylate. MS (m+1)=364. HPLC Peak RT=0.27 minutes (Analytical Method B).

1. customthe reaction was quenched with water
2. additionThe reaction mixture was diluted with ethyl acetate
3. washwashed
4. filtrationfiltered
5. concentrationconcentrated
6. washwashed with H2O
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-dff7b0df98154f23a8fde924ce0afc0b

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399451B2