HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 59420847, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | 1,1-Dimethylethyl 3-hydroxy-3-(2-hydroxy-1,1-dimethylethyl)-1-azetidinecarboxylate | HCID 59420711 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59420847 | HCID 59420847 | 70% |
Reaction Steps
To a solution of tert-butyl 3-hydroxy-3-(1-hydroxy-2-methylpropan-2-yl)azetidine-1-carboxylate (0.20 g, 0.82 mmol) in THF (4 ml) was added in rapid succession, KOtBu (0.19 g, 1.72 mmol) and p-toluenesulfonylchloride (0.16 g, 0.82 mmol) and the solution stirred at room temperature for 90 mins. Water (10 ml) was added and extracted with ethyl acetate. The organic layer was dried (Na2SO4) and concentrated to give an oil. The oil was purified by flash column chromatography eluting with 30 to 70% ethylacetate/hexanes to give the title compound as a colorless oil 0.13 g, 70%. 1H NMR (CDCl3, 400 Mhz) 1.25 (6H, s), 1.45 (9H, s), 3.89 (2H, d), 4.12 (2H, d), 4.20 (2H, s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07767672B2 |
| Source dataset | uspto-grants-2010_08 |
| ORD ID | ord-c2497b44c4634b8b89e0439faee8de78 |
| Source note | uspto-grants-2010_08 |