HuagongsheHuagongshe Chemistry Print Report · For research reference only
(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3,4-dimethyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate → (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-3,4-dimethyl-5,6-dihydropyridine-1(2H)-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3,4-dimethyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate | HCID 89852083 | — |
| Reactant | tert-Butyl (3S,6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-3-hydroxy-4-methyl-1,2,3,6-tetrahydropyridine-1-carboxylate | HCID 89852486 | — |
| Product | (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-3,4-dimethyl-5,6-dihydropyridine-1(2H)-carboxylate | HCID 89852353 | 72% |
Reaction Steps
The title compound was prepared from (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3,4-dimethyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 190, 2.39 g, 6.47 mmol) following the procedure described for Intermediate 8. Silica gel chromatography (0%-20% ethyl acetate/hexanes) afforded the desired product as a colorless oily solid (1.73 g, 72%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09309245B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-17d3a0a682f14c24bdc95021517d2a8f |
| Source note | uspto-grants-2016_04 |