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

HRID 1467993노트

반응식

HRID 1467993 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 8028Tetrahydrofuran용매

실험 절차

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%)

후처리

  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

출처 및 근거

ORD 기록
ord-89143c5012fb4e74b989f2a9b77c262d
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000175B2

반응 노트

불러오는 중…