HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Pentenenitrile → HCID 178446227, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Pentenenitrile | HCID 11604 | — |
| Reactant | Cyclohexyl isocyanide | HCID 79129 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | tert-Butyl 2-oxopiperidine-1-carboxylate | HCID 7577838 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | Pent-4-en-1-amine hydrochloride | HCID 46942242 | — |
| Catalyst | HCID 178449044 | HCID 178449044 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 178446227 | HCID 178446227 | — |
Reaction Steps
To a solution of Boc-piperidinone (1 g, 5 mmol) and tetrabutylammonium cyanate (2.86 g, 10 mmol) in MeOH (12 mL) was added cyclohexyl isocyanide (0.62 mL, 5 mmol) and pent-4-en-1-amine hydrochloride (732 mg, 6 mmol, prepared from the LAH reduction of 4-cyano-butene) in MeOH (8 mL) dropwise. The reaction mixture was stirred at rt for 1.5 h, diluted with EtOAC, washes with aq NaHCO3, brine, dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography (silica gel, EtOAc) to provide the desired product LRMS (M+1)=419.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08399473B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-b3794d42e0e0449699088afa009c9712 |
| Source note | uspto-grants-2013_03 |