4-Pentenenitrile → HCID 178446227、化合物

HRID 1947257

反応式

HRID 1947257 の反応式
[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

参加物

10

反応物 6

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

生成物 1

HCID 178446227HCID 178446227、化合物

試薬・触媒・溶媒 3

HCID 178449044HCID 178449044、化合物触媒HCID 887Methanol溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-b3794d42e0e0449699088afa009c9712
出典データセット
uspto-grants-2013_03
特許番号
US08399473B2

関連ノート

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