HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phenol → 4-[(4-Bromophenyl)-phenoxymethyl]-piperidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phenol | HCID 996 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl azodicarboxylate | HCID 5363146 | — |
| Reactant | Tert-butyl 4-((4-bromophenyl)(hydroxy)methyl)piperidine-1-carboxylate | HCID 57603260 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-[(4-Bromophenyl)-phenoxymethyl]-piperidine-1-carboxylic acid tert-butyl ester | HCID 68970709 | 48% |
Reaction Steps
To a solution of 4-[(4-bromophenyl)-hydroxymethyl]-piperidine-1-carboxylic acid tert-butyl ester (370 mg, 1.00 mmol), phenol (141 mg, 1.50 mmol) and Ph3P (393 mg, 1.50 mmol) in THF (6 mL) at room temperature was added DIAD (0.295 mL, 1.50 mmol) dropwise. The mixture was stirred at room temperature for 2.5 hours. Aqueous work-up and purification gave 4-[(4-bromophenyl)-phenoxymethyl]-piperidine-1-carboxylic acid tert-butyl ester as a colorless oil (213 mg, 48%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07491735B2 |
| Source dataset | uspto-grants-2009_02 |
| ORD ID | ord-ddc8165991964ecba1b7fbd281706e61 |
| Source note | uspto-grants-2009_02 |