Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Naphthol | HCID 8663 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | HCID 67325214 | HCID 67325214 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 53327511 | HCID 53327511 | 39.5% |
Reaction Steps
0.25 g (1.03 mmol) of thiazol-4-ylmethyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate is dissolved in 8 ml of toluene. 0.35 g (1.34 mmol) of triphenylphosphine and 0.16 g (1.13 mmol) of naphth-2-ol are added and then the medium is cooled to 0° C. for slow addition of a solution of 0.27 g (1.34 mmol) of diisopropyl azodicarboxylate in 2 ml of toluene. The medium is stirred at ambient temperature for 14 hours. The residue obtained is taken up in water and extracted twice with dichloromethane. The combined organic phases are washed with a saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated under vacuum. The residue is purified by chromatography on silica gel, elution being carried out with a 99/1 to 98/2 mixture of dichloromethane and methanol. 0.15 g of the expected product is obtained in the form of a powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09000010B2 |
|---|
| Source dataset | uspto-grants-2015_04 |
|---|
| ORD ID | ord-88c6d31ff7ec4b488b1fcca708649087 |
|---|
| Source note | uspto-grants-2015_04 |
|---|