Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Acetate | HCID 517044 | — |
| Reactant | HCID 58550944 | HCID 58550944 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ammonium Chloride | HCID 25517 | — |
| Product | HCID 67469186 | HCID 67469186 | 62% |
Reaction Steps
tert-Butyl 7′-(bromomethyl)-1′-cyano-spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-carboxylate (33.0 mg, 0.0720 mmol) and potassium acetate (35.3 mg, 0.360 mmol) were combined in DMF (0.5 mL) and the mixture was stirred at 80° C. for 18 hours. The mixture was taken up in NH4Cl (10 mL) and was extracted with CH2Cl2 (10 mL). Solvent was removed under reduced pressure and the residue was purified by column chromatrograpy (0-10% EtOAc/CH2Cl2) to obtain tert-butyl 7′-(acetoxymethyl)-1′-cyano-spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-carboxylate (19.5 mg, 62%) as a clear oil. ESI-MS m/z calc. 437.2, found 438.5 (M+1)+; Retention time 2.05 minutes (3 min run).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09365588B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-0c2377d65c3748a885abacb7d93373d3 |
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| Source note | uspto-grants-2016_06 |
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