Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | HCID 59536659 | HCID 59536659 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59536633 | HCID 59536633 | 97.1% |
Reaction Steps
Add HCl (4M in 1,4-dioxane, 52.7 mL, 627 mmol) to a solution of (3S)-3-[1-(6-chloro-2-methyl-3-pyridyloxy)-2-cyclopropyl-ethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (S-1) (13.4 g, 35.2 mmol) in dichloromethane (40.2 mL). Stir under nitrogen at room temperature for 1 h. Evaporate the solvent and dissolve the residue in a mixture of t-butylmethylether (40 mL) and water (40 mL). Separate the phases, wash the aqueous phase with t-butylmethylether (2×). Adjust the pH of the aqueous phase to 9 by the addition of 10% aqueous K2CO3, extract with t-butylmethylether (3×). Wash the combined organic phases with water and brine. Evaporate the volatiles to obtain (3S)-3-[1-(6-chloro-2-methyl-3-pyridyloxy)-2-cyclopropyl-ethyl]-pyrrolidine (S-1) (9.6 g, 97%). MS (m/z)=281.2 [M+1]
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08173821B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-59311ebc8fb54cd1a56e5c223fb52cb5 |
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| Source note | uspto-grants-2012_05 |
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