HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanolamine → HCID 68386798, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanolamine | HCID 700 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (3S)-1-((tert-butoxy)carbonyl)piperidine-3-carboxylic acid | HCID 6951168 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 68386798 | HCID 68386798 | 54.6% |
Reaction Steps
(S)-Piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (500 mg, 2.2 mmol), HATU (833 mg, 2.2 mmol) and Di-isopropylethylamine (761 μL, 4.4 mmol) were stirred in dry DCM (10 ml) in an ice bath for 5 min, then at room temperature for 5 min. Ethanolamine (198 μL, 3.28 mmol) was added and the reaction stirred at room temperature for 3 hrs. The reaction was diluted with DCM (40 ml), washed with water (50 ml), the DCM layer separated and dried (MgSO4) and concentrated. The residue was columned on silica (20 g isolute). Eluting: MeOH/DCM 0-5% 5 CV, MeOH/DCM 5%-5% 10 CV, MeOH/DCM 5-10% 5 CV. TLC visualized with KMnO4. This yielded the product as a clear oil (327 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09249155B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-f8621dbe28394fd0b25fc7300635c1f0 |
| Source note | uspto-grants-2016_02 |