4-Pentenenitrile → HCID 178446227, Verbindung

HRID 1947257

Reaktionsgleichung

Reaktionsgleichung von HRID 1947257
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:15]1([N+:21]#[C-:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.Cl.[CH2:24]([NH2:29])[CH2:25][CH2:26][CH:27]=[CH2:28].[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:36](CCC=C)#[N:37].C([O-])(O)=[O:43].[Na+]>[O-]C#N.C([N+](CCCC)(CCCC)CCCC)CCC.CO.[Cl-].[Na+].O>[CH:15]1([NH:21][C:22]2[C:11]3([CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]3)[N:29]([CH2:24][CH2:25][CH2:26][CH:27]=[CH2:28])[C:36](=[O:43])[N:37]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Komponenten

10

Edukt 6

HCID 116044-PentenenitrileHCID 79129Cyclohexyl isocyanideHCID 516892Sodium BicarbonateHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylateHCID 21226445Aluminium lithium hydrideHCID 46942242Pent-4-en-1-amine hydrochloride

Produkt 1

HCID 178446227HCID 178446227, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178449044HCID 178449044, VerbindungKatalysatorHCID 887MethanolLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. additiondiluted with EtOAC
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (silica gel, EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-b3794d42e0e0449699088afa009c9712
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399473B2

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