Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | P,P-Diphenylphosphinic azide | HCID 199401 | — |
| Reactant | 1-((Tert-butoxy)carbonyl)-3-methylpiperidine-3-carboxylic acid | HCID 18619761 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 20816953 | HCID 20816953 | — |
Reaction Steps
To a suspension of 727 mg (3.0 mmol) rac-3-methyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (CAS: 534602-47-6) in 8 ml toluene was added at ambient temperature 0.42 ml (3.0 mmol) triethylamine. To the resulting solution was added under stirring 0.72 ml (3.3 mmol) diphenylphosphoryl azide and the mixture heated to 90° C. (gas evolution) for 90 min. The reaction mixture was poured onto iced water and extracted 3 times with tert-butyl methyl ether. The combined extracts were washed with brine, dried over sodium sulfate, filtered and evaporated. The title compound was obtained as slightly yellow oil which was used without purification in the next step. MS (m/e): 240 (M).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09067911B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-72bce0149d754feda0be7491fd55cfae |
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| Source note | uspto-grants-2015_06 |
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