Water → HCID 57904830, compound

To a mixture of 1-benzyl-5-((tert-butyldimethylsilyloxy)methyl)piperidine-3-carbaldehyde (3.39 g, 9.75 mmol) in EtOH (50 mL) was added an aqueous solution of NH2OH—HCl (3.75M, 3.12 mL, 11.7 mmol) followed by an aqueous solution of NaOAc (1.5M, 5.2 mL, 7.8 mmol). The reaction mixture was stirred at room temperature for 18 h. H2O (30 mL) was then added and the EtOH was partially removed in vacuo (˜40 mL). The reaction mixture was diluted with ethyl acetate and washed with saturated NaHCO3. The combined aqueous fractions were extracted with ethyl acetate (3×50 mL) and the combined organic fractions were washed with brine and dried (MgSO4) and concentrated in vacuo to afford 3.31 g (94% yield) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.25-7.35 (6 H, m), 3.58 (2 H, d, J=4.5 Hz), 3.43-3.54 (2 H, m), 3.03 (2 H, d, J=4.5 Hz), 2.57-2.68 (1 H, m) 1.90-2.01 (2 H, m), 1.80-1.89 (1 H, m), 1.65-1.77 (2 H, m), 0.93-1.01 (1 H, m). LCMS (+ESI, M+H+) m/z 249.

1. customthe EtOH was partially removed in vacuo (˜40 mL)
2. additionThe reaction mixture was diluted with ethyl acetate
3. washwashed with saturated NaHCO3
4. extractionThe combined aqueous fractions were extracted with ethyl acetate (3×50 mL)
5. washthe combined organic fractions were washed with brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo

ORD record

ord-1faed7c84a3b4124b57bd88dad298cb6

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129398B2