HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonia → Benzyl (2S)-2-carbamoylpiperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (S)-1-N-Cbz-Pipecolinic acid | HCID 688345 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Benzyl (2S)-2-carbamoylpiperidine-1-carboxylate | HCID 27281976 | — |
Reaction Steps
A mixture of (2S)-1-[(benzyloxy)carbonyl]hexahydro-2-pyridinecarboxylic acid (1 eq), TBTU (1.3 eq), DIPEA (1.3 eq), in DMF (2 M) was stirred at R.T. for 30 min then ammonia in dioxane (4 M, 3 eq) was added and stirring was continued for 2 h. The reaction mixture was diluted with EtOAc, washed sequentially with sat. aq. NaHCO3 solution and brine. The solution was dried (Na2SO4), filtered and concentrated under reduced pressure. The crude was purified by crystallization from Et2O giving a white solid. MS (ES) C14H18N2O3 required: 262, found: 263 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08268827B2 |
| Source dataset | uspto-grants-2012_09 |
| ORD ID | ord-ddd6ef74b46c451d9bb6df1a11437a05 |
| Source note | uspto-grants-2012_09 |