HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | 1-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid | HCID 392871 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate | HCID 11065582 | 95% |
Reaction Steps
Add N,O-dimethylhydroxylamine hydrochloride (2.52 g, 26 mmol), 1-hydroxybenzotriazole (HOBt) (2.8 g, 20.8 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI.HCl)(4 g, 20.8 mmol) and 4-methylmorpholine (5.28 g, 52 mmol) at 0° C. to the solution of N-Boc-piperidine-4-carboxylic acid (4 g, 17.4 mmol) in DMF (50 mL), stir the mixture overnight at room temperature. TLC (PE:EtOAc=1:1) shows the reaction is complete. Partition between ethyl acetate and water, collect the organic layer and wash with brine, dry over anhydrous sodium sulfate, filter and concentrate the filtrate under reduced pressure to give the crude product (4.5 g, 95%) which is used in next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359338B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-43b062700b8c48dc8a6efb6c6860a7fb |
| Source note | uspto-grants-2016_06 |