HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | (2S,4R)-1-tert-Butyl 2-methyl 4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylate | HCID 10618477 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate | HCID 11078078 | 85.5% |
Reaction Steps
To a solution of (2S,4R)-4-(tert-butyldimethylsilyloxy)-1-(tert-butoxycarbonyl)-2-methoxycarbonylpyrrolidine (56 g) in tetrahydrofuran (400 ml) was added slowly lithium aluminum hydride (6 g) at 0° C. After stirring for 30 minutes, to the reaction mixture were added dropwise water (6 ml), 4N-aqueous sodium hydroxide (6 ml) and water (18 ml). The precipitate was filtered off, and the solvent was removed in vacuo to give (2S,4R)-4-(tert-butyldimethylsilyloxy)-1-(tert-butoxycarbonyl)-2-hydroxymethylpyrrolidine (44.15 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05102877 |
| Source dataset | uspto-grants-1992_04 |
| ORD ID | ord-0a07a14dba8c40ce801881bacb56a8d5 |
| Source note | uspto-grants-1992_04 |