HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (5-Hydroxymethyl-6-methyl-pyridin-2-yl)-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | tert-butyl N-[5-(2-tert-butylsilyloxypropan-2-yl)-6-methyl-2-pyridinyl]carbamate | HCID 131725830 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (5-Hydroxymethyl-6-methyl-pyridin-2-yl)-carbamic acid tert-butyl ester | HCID 53997211 | 81% |
Reaction Steps
Tetrabutylammonium fluoride (19.6 g, 62.4 mmol) was added to a solution of [5-(tert-butyl-dimethyl-silanyloxymethyl)-6-methyl-pyridin-2-yl]-carbamic acid tert-butyl ester (10.5 g, 31.23 mmol) in THF (100 mL) and stirred at room temperature overnight. Water was added and the product extracted with chloroform. The organic phase was dried and concentrated under reduced pressure. Flash chromatography (MeOH/CH2Cl2, 2.5:77.5) gave (5-hydroxymethyl-6-methyl-pyridin-2-yl)-carbamic acid tert-butyl ester (6.0 g, 81%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07071175B1 |
| Source dataset | uspto-grants-2006_07 |
| ORD ID | ord-1373f99ac6324b0db02b48761b5136e7 |
| Source note | uspto-grants-2006_07 |