Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Di-tert-butyl dicarbonate | HCID 90495 | — |
| Reactant | rel-Methyl (1R,2S,3R,4S)-3-amino-7-oxabicyclo[2.2.1]heptane-2-carboxylate | HCID 89738585 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 89738587 | HCID 89738587 | 92.1% |
Reaction Steps
A solution of (1S,2R,3S,4R)-methyl 3-amino-7-oxabicyclo[2.2.1]heptane-2-carboxylate (11) (500 mg, 2.4 mmol), Et3N (0.85 ml, 6 mmol) and BOC2O (0.66 ml, 2.88 mmol) in acetonitrile was stirred at rt for 2 h and then heated at 80° C. for 30 min when TLC confirmed completion of reaction. Acetonitrile was removed and the crude product was purified by column chromatography using silica gel (100-200 mesh) to afford the desired compound (600 mg, 92%) as a colourless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09238656B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-56f1d53e5692499fb547b8ddc7e5ddf1 |
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| Source note | uspto-grants-2016_01 |
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