Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 4-Aminotetrahydropyran | HCID 419223 | — |
| Reactant | Methyl 3-formylbenzoate | HCID 639145 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 90238065 | HCID 90238065 | 67% |
Reaction Steps
To a solution of methyl 3-formylbenzoate (492 mg, 3.0 mmol) in MeOH (10 mL) was added tetrahydro-2H-pyran-4-amine (303 mg, 3.0 mmol) and AcOH (0.05 mL). The mixture was stirred at 25° C. for 2 h. NaBH3CN (945 mg, 15.0 mmol) was added, and the resulting mixture was stirred at 25° C. for 16 h. The reaction solution was concentrated and the residue was dissolved in water and extracted with DCM. The organic layer was concentrated, and the residue was purified by prep-TLC to give the title product (500 mg, Yield 67%). LCMS (m/z): 250.1 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09365519B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-e0efae27f6394b29a482bc446bdb308f |
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| Source note | uspto-grants-2016_06 |
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