Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 3-Amino-4-hydroxybenzonitrile | HCID 271258 | — |
| Reactant | tert-Butyl 4-oxopiperidine-1-carboxylate | HCID 735900 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59444107 | HCID 59444107 | 87% |
Reaction Steps
Polymer supported sodium cyanoborohydride (3531 mg, 7.20 mmol, 2.04 mmol/g) was added to a solution of 3-amino-4-hydroxybenzonitrile (D19, 477 mg, 3.56 mmol), 1,1-dimethylethyl 4-oxo-1-piperidinecarboxylate (709 mg, 3.56 mmol) and acetic acid (1 mL, 17.5 mmol) in tetrahydrofuran (10 mL). The mixture was heated by microwave at 100° C. for 30 min and then for a further 30 min before being filtered and concentrated by rotary evaporation to give 1,1-dimethylethyl 4-[(5-cyano-2-hydroxyphenyl)amino]-1-piperidinecarboxylate (D32, 982 mg, 3.09 mmol, 87% yield) as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08426443B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-3f36f2d48f7c4e3b897c8cfdee077383 |
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| Source note | uspto-grants-2013_04 |
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