Buchwald–Hartwig amination: Methyl 3-bromobenzoate → Methyl 3-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}benzoate
14% yield, run at 100 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | Methyl 3-bromobenzoate | C₈H₇BrO₂ | |
| Reactant | 4-(N-Boc-amino)piperidine | C₁₀H₂₀N₂O₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | Methyl 3-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}benzoate | C₁₈H₂₆N₂O₄ | 13.76% |
Conditions
- Temperature
- 100 °C
Yield
- 14% of Methyl 3-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}benzoate.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
Procedure
Copied from the source record, unedited
All chemicals were mixed in a 50 mL round bottom flask. The solids were degassed and placed under nitrogen. Toluene was added and the mixture was stirred at 100°C for 24 h. Cooled and filtered. The filtrate was concentrated under vacuum. Crude product was mainly starting material but some product had been formed. The product was purified by silica gel chromatography using 1-4% methanol/DCM. Product was slightly more polar than starting material bromide. There was obtained 230 mg of the desired product as a solid. HNMR and LC MS ok.
The source
This record comes from experimental reaction archive (ord-2de77de369ef42f8b910f9e83130f454). Open the source and check it against what is on this page.
experimental reaction archive record ord-2de77de369ef42f8b910f9e83130f454 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
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Where to next
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