HuagongsheHuagongshe Chemistry Print Report · For research reference only
Oxazole → HCID 68971731, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Oxazole | HCID 9255 | — |
| Reactant | tert-Butyl 4-formylpiperidine-1-carboxylate | HCID 1514430 | — |
| Reactant | Borane;tetrahydrofuran | HCID 2723981 | — |
| Reactant | HCID 178418306 | HCID 178418306 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68971731 | HCID 68971731 | 71.5% |
Reaction Steps
To a solution of oxazole (420 mg, 6.08 mmol) in THF (15 mL) was added BH3-THF (1.0M in THF, 6.69 mL, 6.69 mmol). The mixture was stirred at room temperature for 1 hour. After cooling to −78° C., t-BuLi (1.7M, 4.29 mL, 7.30 mmol) was introduced to the mixture and stirred at this temperature for 30 min. 4-Formyl-piperidine-1-carboxylic acid tert-butyl ester (1.30 g, 6.08 mmol) was added dropwise and the mixture was stirred at −78° C. for 3 hours. Work-up and purification gave 4-(hydroxy-oxazol-2-yl-methyl)-piperidine-1-carboxylic acid tert-butyl ester as a white foam (1.227 g, 71%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07491735B2 |
| Source dataset | uspto-grants-2009_02 |
| ORD ID | ord-835ecd3af05a409a89e17b45104d0923 |
| Source note | uspto-grants-2009_02 |