Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | Methyl 2-(3-cyanopyridin-4-YL)acetate | HCID 53419517 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 66803790 | HCID 66803790 | 22.42% |
Reaction Steps
NaBH4 (228 mg, 6.023 mmol) was added portion wise over a period of 20 minutes to a solution of methyl 2-(3-cyanopyridin-4-yl)acetate (I-65a: 530 mg, 3.011 mmol) in ethanol (6 mL) at 0° C. and the resulting reaction mass was stirred at 0° C. for 4 hours. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mass was quenched with saturated NH4Cl solution and extracted using ethyl acetate. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (2% methanol in DCM) afforded 100 mg of the product (22.42% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08946260B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-67014bf1087648f1b7d9ef2fe1900c37 |
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| Source note | uspto-grants-2015_02 |
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