HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (R)-4-Cyclohexyl-oxazolidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | (2R)-2-amino-2-cyclohexylethan-1-ol | HCID 13617488 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (R)-4-Cyclohexyl-oxazolidin-2-one | HCID 13347633 | — |
Reaction Steps
To a solution of (R)-2-Amino-2-cyclohexyl-ethanol.HCl salt (1.0 g, 5.57 mmol, 1.0 equiv) in CH2Cl2 (30.0 mL) at 0° C. was added DIPEA (1.94 mL, 11.1 mmol, 2.0 equiv) followed by triphosgene (4.95 g, 16.7 mmol, 3.0 equiv) and the resulting solution was stirred at room temperature for 12 hours. The solution was then concentrated and the residue was diluted with EtOAc. The solution was washed with water, brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography, (EtOAc 100%) to give product 520 mg.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09040690B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-843538dc912c4361ab50ed643abc0dd7 |
| Source note | uspto-grants-2015_05 |