HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → tert-Butyl cis(+/-)-4-(benzylamino)-[(2E)-2-buten-1-yloxy]piperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | tert-Butyl 3-[(2E)-2-buten-1-yloxy]-4-oxopiperidine-1-carboxylate | HCID 67548695 | — |
| Product | tert-Butyl cis(+/-)-4-(benzylamino)-[(2E)-2-buten-1-yloxy]piperidine-1-carboxylate | HCID 86648623 | 99% |
Reaction Steps
The same operation as in Example (90c) was performed using tert-butyl 3-[(2E)-2-buten-1-yloxy]-4-oxopiperidine-1-carboxylate obtained in Example (119b) (5 g, 16 mmol), benzylamine (2.04 g, 19 mmol), sodium (triacetoxy)borohydride (7.41 g, 35 mmol) and 1,2-dichloroethane (50 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1, 1/1, 1/3, 0/1) to obtain 5.74 g of the title compound as a colorless solid (99%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08536197B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-1478f796eba04961951eebd0f4c3c6e7 |
| Source note | uspto-grants-2013_09 |