Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dibutyltin oxide | HCID 61221 | — |
| Reactant | Azidotrimethylsilane | HCID 78378 | — |
| Reactant | HCID 86641749 | HCID 86641749 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 178494887 | HCID 178494887 | — |
Reaction Steps
To a solution of tert-butyl (3R,4S)-3-([[3-[(4-cyanobenzyl)oxy]-5-(3-methoxy-propyl)benzyl](cyclopropyl)amino]carbonyl}-4-{4-[2-(2,6-dichloro-4-methylphen-oxy)ethoxy]phenyl}piperidine-1-carboxylate (1 eq.) from the previous step in toluene (0.04 M) was added azido(trimethyl)silane (3 eq.) and dibutyltin oxide (0.25 eq.). The reaction was heated to 105° C. and stirred for 16 h. The volatiles were removed in vacuo and the crude product was purified by flash column chromatography (SiO2, 95.9:3.9:0.2 (v/v/v) DCM/MeOH/AcOH) to afford the title compound as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08343968B2 |
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| Source dataset | uspto-grants-2013_01 |
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| ORD ID | ord-11121ada6421448c9e09c16dbd82627e |
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| Source note | uspto-grants-2013_01 |
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