HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrabutylammonium Fluoride → 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-3-methylpyridin
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-methylpyridin | HCID 131725827 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-3-methylpyridin | HCID 22036037 | 59.4% |
Reaction Steps
Tetrabutylammonium fluoride (25.1 g 79.6 mmol) was added to a solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-methylpyridin (18.0 g, 39.8 mmol) in THF (150 mL). The reaction mixture was stirred overnight at room temperature. Concentration under reduced pressure followed by flash chromatography (hexane/EtOAc, 50:50) gave 2-[N,N -bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-3-methylpyridin (8.0 g, 59%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07071175B1 |
| Source dataset | uspto-grants-2006_07 |
| ORD ID | ord-7f016dac5a71499cab1442bd665fa2a5 |
| Source note | uspto-grants-2006_07 |