Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | HCID 89515406 | HCID 89515406 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 89514376 | HCID 89514376 | 74% |
Reaction Steps
A solution of 2-acetamido-N-tert-butyl-2-(3-chloropropyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamide (0.39 g, 0.9 mmol) in acetonitrile was treated with NaI (10% mol) and pyrolidine (0.75 mL, 9 mmol). The mixture was warmed to 50° C. and stirred overnight. After cooling to room temperature, the reaction was diluted with water, extracted with dichloromethane, dried over MgSO4, and concentrated to give crude 2-acetamido-N-tert-butyl-2-(3-(pyrrolidin-1-yl)propyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamide (0.31 g). This material was used in the next step without further purification. ESI MS found for C25H48BN3O4 m/z [466.6 (M+1)].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09266908B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-939b1ccc95384e41a726ff1242342fce |
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| Source note | uspto-grants-2016_02 |
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