Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Methyl chloroformate | HCID 6586 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 131726321 | HCID 131726321 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 68883845 | HCID 68883845 | 93% |
Reaction Steps
(S)-2-methyl-2-(3-piperidin-3-yl-phenoxy)-propionic acid benzyl ester-L-(+)-tartrate salt (Preparation 3, Method F; 119 mg, 0.24 mmol) was dissolved in 2 mL methlyene chloride and 1 mL water. Sodium bicarbonate (79 mg, 0.95 mmol) and methyl chloroformate (37 mL, 0.47 mmol) were added, and the biphasic mixture and resulting mixture stirred at ambient temperature for 2 h. The mixture was diluted with water (50 mL), acidified with 1N aqueous hydrochloric acid and extracted with diethyl ether (2×50 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to provide 90 mg (93%) of (S)-3-[3-(1-Benzyloxycarbonyl-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid methyl ester as a clear oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07199243B2 |
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| Source dataset | uspto-grants-2007_04 |
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| ORD ID | ord-ab3b2bd2a45141e88141a5b710a9d78d |
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| Source note | uspto-grants-2007_04 |
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