Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | tert-butyl (4S,5R)-4-formyl-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate | HCID 10966732 | — |
| Reactant | (1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one | HCID 136023029 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 275387-85-4 | HCID 12970128 | — |
Reaction Steps
To a solution of (4S,5R)-N-Boc-2,2,5-trimethyl-oxazolidine-4-carbaldehyde (1.52 g, 5.43 mmol) (Example 102A above) and dimethyl(1-diazo-2-oxopropyl)phosphonate (1.57 g, 8.15 mmol) in dry MeOH (30 mL) was added K2CO3 at 0° C. The mixture was stirred at 0° C. for 30 min and room temperature for 20 h. After addition of saturated aqueous NH4Cl and EtOAc, the organic layer was separated and aqueous layer was extracted with EtOAc (3×). The ethyl acetate layers were combined and dried with MgSO4. The crude material was purified by flash column chromatography eluting with EtOAc/hexanes (1:6) to give (4R,5R)-N-Boc-2,2,5-Trimethyl-4-ethynyl-oxazolidine. (Yield 0.97 g, 65%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06252086B1 |
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| Source dataset | uspto-grants-2001_06 |
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| ORD ID | ord-6368348e69b846a1b8c5eef9d0dac20f |
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| Source note | uspto-grants-2001_06 |
|---|
