HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Methoxide → {1-[2-((3S,4S)-4-Hydroxy-3-methyl-piperidin-1-yl)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Reactant | 2,2-Dimethyl-propionic acid (3S,4S)-1-[2-(4-tert-butoxycarbonylamino-piperidin-1-yl)-ethyl]-3-methyl-piperidin-4-yl ester | HCID 66841300 | — |
| Product | {1-[2-((3S,4S)-4-Hydroxy-3-methyl-piperidin-1-yl)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester | HCID 67523806 | — |
Reaction Steps
Crude 15 (8.2 g, 19.27 mmol) is treated with NaOMe (0.5M in methanol, 77 ml, 38.5 mmol) and heated under reflux for 24 hours. The solvent is then evaporated, the residue taken up in DCM and extracted with 1N-NaOH and brine. Drying and evaporation gave a brown oil which is purified by chromatography on silicagel using DCM (saturated with ammonia) and MeOH (from 1% to 5%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08183366B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-293744f074ca40c19243d415879dcdc0 |
| Source note | uspto-grants-2012_05 |