HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → trans(+/-)-Benzyl 3-(bis(tert-butoxycarbonyl)amino)-4-hydroxypiperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Di-tert-butyl dicarbonate | HCID 90495 | — |
| Reactant | Benzyl (3R,4R)-3-(tert-butoxycarbonylamino)-4-hydroxypiperidine-1-carboxylate | HCID 53487823 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | trans(+/-)-Benzyl 3-(bis(tert-butoxycarbonyl)amino)-4-hydroxypiperidine-1-carboxylate | HCID 131729680 | — |
Reaction Steps
To a solution of trans (+/−)-benzyl 3-(tert-butoxycarbonylamino)-4-hydroxypiperidine-1-carboxylate (1.0 equiv.) in DCM and CH3CN (1:1, 0.14 M) was added BOC2O (1.0 equiv.), triethylamine (1.5 equiv.), and DMAP (catalytic amount). The reaction was stirred at room temperature for 15 h, upon which time the solution was concentrated and purified via silica gel column chromatography eluting with EtOAc and hexanes (1:6) to give the desired product as a white foam. LCMS (m/z): 451.1 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08829193B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-3db9196d8f9649a7a5062afe34a717b4 |
| Source note | uspto-grants-2014_09 |