Formaldehyde → HCID 84766055, compound

To a solution of 2-ethylpiperidine-2-carboxylic acid (320 mg, 1.65 mmol) in MeOH (4.0 mL) and water (4.0 mL) was added paraformaldehyde (372 mg, 4.13 mmol) and Pd/C (10%) (88 mg, 0.83 mmol). One equivalent of sodium carbonate (175 mg, 1.65 mmol) was added and the reaction mixture was stirred under a hydrogen atmosphere at room temperature for overnight. LC/MS indicated complete conversion of starting material. The reaction mixture was filtered through diatomaceous earth. The filter cake was washed with MeOH (2×30 mL). The filtrate was concentrated in vacuo to give the crude product. The crude solid was suspended in methanol (50 mL) and the resulting suspension was filtered and the filtrate was concentrated to give 2-ethyl-1-methylpiperidine-2-carboxylic acid (202 mg, 71.4%) as a solid. LC/MS: 172 (M+1); 1H NMR (400 MHz, CD3OD) δ ppm 3.58 (td, J=12.80, 3.51 Hz, 1 H), 3.09-3.20 (m, 1H), 2.81 (s, 3H), 2.17-2.29 (m, 1H), 1.54-1.84 (m, 7H), 0.98 (t, J=7.40 Hz, 3H).

1. filtrationThe reaction mixture was filtered through diatomaceous earth
2. washThe filter cake was washed with MeOH (2×30 mL)
3. concentrationThe filtrate was concentrated in vacuo
4. customto give the crude product
5. filtrationthe resulting suspension was filtered
6. concentrationthe filtrate was concentrated

ORD record

ord-7bbada23a6784fb5831d6c41b0a373dc

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09427479B2