Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diphosgene | HCID 10426 | — |
| Reactant | Tetrahydro-4H-pyran-4-ol | HCID 74956 | — |
| Reactant | 4-Amino-1-N-Cbz-piperidine | HCID 17846640 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 118037570 | HCID 118037570 | — |
Reaction Steps
Benzyl 4-aminopiperidine-1-carboxylate (100 mg) is dissolved in toluene (1 mL), treated dropwise with a solution of diphosgene (52 μL) in toluene (1 mL) and stirred for 12 hours at 80° C. Tetrahydro-2H-pyran-4-ol (41 μL) is added and the mixture is heated for 3 hours at 80° C. The mixture is partitioned between ethylacetate and saturated aqueous NH4Cl solution. The organic phase is dried (MgSO4) and concentrated. The residue is purified by HPLC on reversed phase to give the title compound. LC (method 1): tR=0.95 min; Mass spectrum (ESI+): m/z=363 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09187477B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-8e63531bb23747b7a5a62b9716448a75 |
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| Source note | uspto-grants-2015_11 |
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