4-Pentenenitrile → HCID 178446227, 화합물

HRID 1947257

반응식

HRID 1947257 반응식
[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

참가 물질

10

반응물 6

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

생성물 1

HCID 178446227HCID 178446227, 화합물

시약·촉매·용매 3

HCID 178449044HCID 178449044, 화합물촉매HCID 887Methanol용매2회HCID 57417360Sodium chloride; water용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-b3794d42e0e0449699088afa009c9712
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399473B2

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