Sodium Iodide → tert-Butyl 3-(azidomethyl)piperidine-1-carboxylate

HRID 1478589노트

반응식

HRID 1478589 반응식
S(O[CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1)(C1C=CC(C)=CC=1)(=O)=O.[N-:26]=[N+:27]=[N-:28].[Na+].[Na+].[I-]>CN(C=O)C>[N:26]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1)=[N+:27]=[N-:28]

참가 물질

5

반응물 3

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 18369320Tert-butyl 3-((P-tolylsulfonyloxy)methyl)piperidine-1-carboxylate

생성물 1

HCID 22647380tert-Butyl 3-(azidomethyl)piperidine-1-carboxylate수율 93.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

tert-butyl 3-((tosyloxy)methyl)piperidine-1-carboxylate (8.85 g, 24 mmol) was dissolved in DMF (100 ml), and then NaN3 (6.24 g, 96 mmol) and NaI (0.36 g, 2.40 mmol) were added, followed by stirring at 70° C. for hours. After the completion of the reaction, the reaction mixture was extracted with H2O, EA, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (EA:Hex=1:10), to give tert-butyl 3-(azidomethyl)piperidine-1-carboxylate (5.38 g, 92%).

후처리

  1. customAfter the completion of the reaction
  2. extractionthe reaction mixture was extracted with H2O, EA, and brine
  3. customby drying
  4. filtration(Na2SO4), filtration, and concentration under reduced pressure
  5. customthe residue was purified by column chromatography (EA:Hex=1:10)

출처 및 근거

ORD 기록
ord-cd12c09ff1d5406b9f302d2ee11c55ec
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403831B2

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