N'-Hydroxy-2-methylpropanimidamide → 1-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidin-4-OL

HRID 1467993ノート

反応式

HRID 1467993 の反応式
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]#[N:9])[CH2:4][CH2:3]1.[OH:10]/[N:11]=[C:12](/N)\[CH:13]([CH3:15])[CH3:14]>C1COCC1.[Cl-].[Cl-].[Zn+2]>[CH:13]([C:12]1[N:9]=[C:8]([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)[O:10][N:11]=1)([CH3:15])[CH3:14]

参加物

5

反応物 2

HCID 5712089N'-Hydroxy-2-methylpropanimidamideHCID 218978254-Hydroxypiperidine-1-carbonitrile

生成物 1

HCID 218977441-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidin-4-OL

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 4-hydroxypiperidine-1-carbonitrile (0.4 g, 3.1 mmol) in THF (10 mL), (E)-N′-hydroxyisobutyrimidamide (0.35 g, 35 mmol) and ZnCl2 (1M solution in THF) (4.7 mL) were added and stirred at room temperature for 10 h. The reaction mixture was concentrated in vacuo and the resulting crude was dissolved in 4N HCl in ethanol-water (1:1) and stirred at 60-70° C. for 2-3 h. The reaction was quenched by saturated NaHCO3 and the organic layer was separated and concentrated. The residue on column chromatography gave the title compound. (0.280 g, 41.8%)

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe resulting crude was dissolved in 4N HCl in ethanol-water (1:1)
  3. stirringstirred at 60-70° C. for 2-3 h
  4. customThe reaction was quenched by saturated NaHCO3
  5. customthe organic layer was separated
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-89143c5012fb4e74b989f2a9b77c262d
出典データセット
uspto-grants-2015_04
特許番号
US09000175B2

反応ノート

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