HuagongsheHuagongshe Chemistry Print Report · For research reference only
Isopropanol → 1,1-dimethylethyl (3R,4S)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Isopropanol | HCID 3776 | — |
| Reactant | Tert-butyl 3-(benzyloxycarbonylaminomethyl)-4-hydroxy-piperidine-1-carboxylate | HCID 68810490 | — |
| Solvent | Carbon Dioxide | HCID 280 | — |
| Product | 1,1-dimethylethyl (3R,4S)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate | HCID 86635364 | — |
| Product | 1,1-dimethylethyl (3S,4R)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate | HCID 86635365 | — |
Reaction Steps
1,1-Dimethylethyl 4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate was resolved via supercritical fluid chromatography (SFC) using a Chiralpak AD-H 30×250 mm column (20% Isopropanol in CO2; 70 ml/min; 30 deg C.; uv 220 nm) to obtain the E1 (first eluting isomer: 98% ee) and E2 (second eluting isomer; 94% ee) enantiomers presumed 1,1-dimethylethyl (3S,4R)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate (E2) and presumed 1,1-dimethylethyl (3R,4S)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate (E1) as white solids.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08071592B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-41af00076c374fb481be0e84c590c566 |
| Source note | uspto-grants-2011_12 |