Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 3-(Chloromethyl)pyridine hydrochloride | HCID 23394 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 22885690 | HCID 22885690 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 44415947 | HCID 44415947 | — |
Reaction Steps
To a solution of 75 mg of non-racemic 1-(S)-(1-(R)-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-2-(S)-(4-fluorophenyl)-3-(R)-aminocyclopentane from Example 39 in 2 mL of acetonitrile was added 34 mg of 3-picolyl chloride hydrochloride and 0.090 mL of DIPEA. The reaction was heated at 50° C. for 3 days and then poured into water and extract twice with ethyl acetate. The organic layers were washed with a portion of brine, combined, dried over sodium sulfate and evaporated. The residue was purified on a 3×1 mm preparative silica gel plates eluted with 5% methanol in methylene chloride to give 40 mg of title compound as an oil. Mass spec (NH3 /CI): 527 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05750549 |
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| Source dataset | uspto-grants-1998_05 |
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| ORD ID | ord-36c9949d4bc14c148733f57e865f8271 |
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| Source note | uspto-grants-1998_05 |
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