Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-(4-Nitro-phenoxycarbonyloxy)-piperidine-1-carboxylic acid 6-[(4-phenoxy-phenyl)-oxycarbonylamino]-hexyl ester | HCID 15293307 | — |
| Reactant | 8-Azaspiro(4.5)decane hydrochloride | HCID 22401229 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67683117 | HCID 67683117 | 82.4% |
Reaction Steps
A solution of 8-aza-spiro[4.5]decane hydrochloride (791 mg, 4.50 mmol) and triethylamine (2.24 mL, 16.1 mmol) in 20 mL of anhydrous dimethylformamide was added under nitrogen dropwise to a solution of the carbonate prepared in Example 5 (2.00 g, 3.22 mmol) in 25 mL of anhydrous dimethylformamide. After the addition the reaction was stirred at room temperature overnight. The reaction was diluted with ethyl acetate, extracted one time with 1N HCl, multiple times with saturated Na2CO3 and then water, dried (MgSO4) and the solvent removed under reduced pressure to give 1.65 g of an oil. Purification of the oil on silica gel (230-400 mesh) using 20% ethyl acetate-methylene chloride as the eluent gave 1.01 g (52%) of the title compound as a light yellow oil, MS [M+H]+ 622.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05527804 |
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| Source dataset | uspto-grants-1996_06 |
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| ORD ID | ord-81abfca44c954bb2a48ed2365b50d137 |
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| Source note | uspto-grants-1996_06 |
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