Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 58315456 | HCID 58315456 | — |
| Catalyst | Iron | HCID 23925 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 58315448 | HCID 58315448 | 94% |
Reaction Steps
To a suspension of 5-[3-(tert-butyl-dimethyl-silanyloxy)-azetidin-1-yl]-2-nitro-pyridine (124 mg, 0.401 mmol) in 5 mL of ethanol is added iron powder (206 mg, 3.68 mmol) then 2 mL of NH4Cl solution. The resulting mixture is heated at 80° C. for 3 h and filtered through celite and concentrated. The resulting dark solid is divided between ethyl acetate and water. The aqueous phase is extracted with ethyl acetate (2×50 mL). The combine organic layers are ished with brine, dried over Na2SO4 and concentrated to give 5-[3-(tert-butyl-dimethyl-silanyloxy)-azetidin-1-yl]-pyridin-2-ylamine (105 mg, 94%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08685980B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-5fa6b82ff3f6463480f2ecefc0c005f5 |
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| Source note | uspto-grants-2014_04 |
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