Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1-Butanol | HCID 263 | — |
| Reactant | Potassium bis(trimethylsilyl)amide | HCID 3251421 | — |
| Reactant | HCID 135816345 | HCID 135816345 | — |
| Product | Ammonia | HCID 222 | — |
| Product | HCID 135816376 | HCID 135816376 | 59% |
Reaction Steps
Potassium bis(trimethylsilyl)amide (35 mg, 0.176 mmol) was added to a solution of the title compound of Example 146 (80 mg, 0.145 mmol) in n-butanol (2 ml), and the reaction stirred at 110° C. for 6½ hours. The cooled mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate (20 ml) and sodium bicarbonate solution (10 ml). The phases were separated, the organic layer washed with additional sodium bicarbonate solution (10 ml), brine (10 ml), dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (100:0:0 to 99.6:0.4:0.5) to afford the title compound (50 mg, 59%) as a white foam.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06458951B2 |
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| Source dataset | uspto-grants-2002_10 |
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| ORD ID | ord-261b172dc13f4a8989b7838d29a160e9 |
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| Source note | uspto-grants-2002_10 |
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