Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-(Diphenylmethyl)azetidin-3-yl methanesulfonate | HCID 2758716 | — |
| Reactant | HCID 9999760 | HCID 9999760 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 90416740 | HCID 90416740 | 18.9% |
Reaction Steps
To a suspension of (1R)-1-[(3S,4S)-1-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]carbonyl}-4-(4-methoxy-3-hydroxyphenyl)-3-methylpyrrolidin-3-yl]ethanol (2.0 g) and potassium carbonate (1.46 g) in acetonitrile (30 mL) is added 1-(diphenylmethyl)azetidin-3-yl methanesulfonate (2.51 g). The mixture is heated at 80° C. overnight. Cool the reaction mixture and pour into ethyl acetate (100 mL), wash with water (40 mL) and brine (40 mL), dry over sodium sulfate, filter and evaporate the filtrate to dryness. Purify the resulting residue (silica gel, 60% ethyl acetate/hexanes to ethyl acetate) to provide 0.6 g of the title compound. MS (ES+)=601 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09034864B2 |
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| Source dataset | uspto-grants-2015_05 |
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| ORD ID | ord-1c08244a57df484888e1169c87cdc89a |
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| Source note | uspto-grants-2015_05 |
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