HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hexane → 1-(1,1-Dimethylethyl) 3-ethyl 4-oxo-1,3-piperidinedicarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hexane | HCID 8058 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Di-tert-butyl dicarbonate | HCID 90495 | — |
| Reactant | 4-Oxo-piperidine-3-carboxylic acid ethyl ester | HCID 107316 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-(1,1-Dimethylethyl) 3-ethyl 4-oxo-1,3-piperidinedicarboxylate | HCID 6420876 | 95.4% |
Reaction Steps
To a solution of ethyl 4-oxopiperidine-3-carboxylate (180.0 g, 0.87 mol, 1.0 eq.) in DCM (2.7 L) was added Et3N (352.14 g, 3.48 mol, 4.0 eq.) dropwise at 15° C. and stirred for 30 min followed by addition of (BOC)2O (210.0 g, 0.96 mol, 1.10 eq.) maintaining the temperature below 10° C. The resulted mixture was stirred at rt overnight, and concentrated to give a crude product that was stirred with hexane (3.5 L) for 1 h and filtered. The filtered cake was washed with hexanes. The combined organic phase was concentrated to furnish the title compound (226.0 g, 0.83 mol, 95.4%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09255096B1 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-7ca7a6158f554644964c681c9531b5f6 |
| Source note | uspto-grants-2016_02 |