HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 4-(1,1-Dimethylethyl) 1-(phenylmethyl) 2-(hydroxymethyl)-1,4-piperazinedicarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Borane | HCID 6331 | — |
| Reactant | N-4-Boc-N-1-Cbz-2-piperazine carboxylic acid | HCID 2756777 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-(1,1-Dimethylethyl) 1-(phenylmethyl) 2-(hydroxymethyl)-1,4-piperazinedicarboxylate | HCID 23531039 | 92% |
Reaction Steps
To 1-[(benzyloxy)carbonyl]-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (1 g) in anhydrous THF (11 ml) under argon, cooled to 0° C. was added 1M borane in THF (11 ml) and the mixture allowed to warm to room temperature over 3.5 hours. After cooling to 0° C., MeOH was added and stirring continued for 72 hours. The solvents were evaporated, saturated aqueous sodium bicarbonate and ethyl acetate added, the organic phase dried (MgSO4) and evaporated to give the title compound (0.88 g, 92%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08710224B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-2193abe0ede94f3c972a318ead6ee0bb |
| Source note | uspto-grants-2014_04 |