Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Tosylmethyl isocyanide | HCID 161915 | — |
| Reactant | (3aS,8aR)-7-Methyl-1,2,3,3a,7,8a-hexahydro-3b,7,8-triaza-cyclopenta[a]inden-6-one | HCID 67379018 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67378655 | HCID 67378655 | 94% |
Reaction Steps
Sodium hydride (95%, 112 mg, 4.44 mmol) is suspended in 3 mL of anhydrous THF, and then a mixture of (3aS,8aR)-7-Methyl-1,2,3,3a,7,8a-hexahydro-3b,7,8-triaza-cyclopenta[a]inden-6-one (283 mg, 1.48 mmol) and p-toluenesulfonylmethyl isocyanide (97%, 347 mg, 1.77 mmol) in 5 mL of anhydrous THF is added dropwise. The mixture is stirred at room temperature for an hour, and then quenched with water. The mixture is extracted with CH2Cl2 (5×10 mL). The combined organic phase is washed with brine, and then dried with anhydrous Na2SO4. After filtration, the filtrate is evaporated to dryness under reduced pressure to give crude product (320 mg, yield 94%) as brown solids, which is used for the next reaction without further purification. MS (ESI) m/z 231.1 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08664207B2 |
|---|
| Source dataset | uspto-grants-2014_03 |
|---|
| ORD ID | ord-8b3379aba6824c2ba9d4af5816ce3efc |
|---|
| Source note | uspto-grants-2014_03 |
|---|