Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzyl Alcohol | HCID 244 | — |
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Phosgene | HCID 6371 | — |
| Reactant | HCID 68529807 | HCID 68529807 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 68530198 | HCID 68530198 | 47% |
Reaction Steps
To a solution of Compound 51 (1.21 g, 2 mmol), 4-dimethylaminopyridine (244 mg, 2 mmol) and pyridine (1.62 mL, 20 mmol) in dichloromethane (20 mL) at −10° C. was added phosgene (20% in toluene, 2.10 mL, 4 mmol) dropwise. The resulting mixture was stirred for 15 minutes at −10° C. Benzyl alcohol (0.83 mL, 8 mmol) was added and the resulting mixture was stirred at 21° C. for 2 hours. The reaction was quenched with saturated sodium bicarbonate solution, and aqueous layer was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated to afford yellow oil, which was chromatographed to give the desired product (Yield: 47%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07687496B2 |
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| Source dataset | uspto-grants-2010_03 |
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| ORD ID | ord-7c494ff28d2c49eb9381a429b1b588b7 |
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| Source note | uspto-grants-2010_03 |
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