4-Pentenenitrile → HCID 178446227, compound

HRID 1947257Notes

Reaction equation

HRID 1947257 reaction equation
[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

Participants

10

Reactant 6

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

Product 1

HCID 178446227HCID 178446227, compound

Reagents, catalysts & solvents 3

HCID 178449044HCID 178449044, compoundCatalystHCID 887MethanolSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-b3794d42e0e0449699088afa009c9712
Source dataset
uspto-grants-2013_03
Patent number
US08399473B2

Reaction notes

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