HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phenol → HCID 90405868, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phenol | HCID 996 | — |
| Reactant | tert-Butyl (2S)-2-(((4-methylbenzene-1-sulfonyl)oxy)methyl)pyrrolidine-1-carboxylate | HCID 11783214 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | (R)-tert-butyl 3-hydroxy-3-(3-hydroxyphenyl)propylcarbamate | HCID 90405310 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 90405868 | HCID 90405868 | — |
Reaction Steps
A mixture of (S)-tert-butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate (1.6 g, 5.4 mmol), phenol (7, Intermediate I) (0.8 g, 2.9 mmol), t-BuO−K+ (0.5 g, 4.5 mmol) in anhydrous DMF (5 mL) was heated at +45° C. for 16 hrs. The reaction mixture was concentrated under reduced pressure, partitioned between EtOAc and 5% NaOH, organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure. Purification by column chromatography gave (S)-tert-butyl 2-((3-((R)-3-((tert-butoxycarbonyl)amino)-1-hydroxypropyl)phenoxy)methyl)pyrrolidine-1-carboxylate as a light yellow oil. Yield (0.8 g, 59%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09133154B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-c8cbe2f514794d03ba127febf730f06f |
| Source note | uspto-grants-2015_09 |