HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | (alphaR)-alpha-[(1S)-2-(Dimethylamino)-1-methylethyl]-alpha-ethyl-3-methoxybenzenemethanol | HCID 9942979 | — |
| Reactant | Talabostat mesylate | HCID 11522448 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | (2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol hydrochloride | HCID 25146677 | — |
Reaction Steps
(2S,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol (754.1 g, 3 mol, ee 95%) were dissolved in acetone (5 L) in a 10 L double jacket vessel equipped with an electrical impeller stirrer, a gas transition line, Pt100 temperature measuring equipment and an oil based cooling/heating system. Hydrogen chloride (110 g, 3.0 mol) was transferred within 15 minutes at a temperature of 15° C. through the reaction mixture. The reaction mixture was cooled to 0° C. to 5° C. and after 24 hours at that temperature siphoned off. The product was stored at 40° C. and 10 mbar for 14 hours in a drying oven. (2S,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol hydrochloride was obtained as a colorless solid (722.3 g, 83.7%, ee 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08877974B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-cad94cb148f243ecaae573cd2e83d2bd |
| Source note | uspto-grants-2014_11 |