Water → cis-4-Azidomethyl-1-tert-butoxycarbonyl-3-hydroxypiperidine

HRID 344291노트

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HRID 344291 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([CH2:14]OS(C)(=O)=O)[C@H:10]([OH:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:21]=[N+:22]=[N-:23].[Na+].[Cl-].[NH4+].O>CN(C)C=O>[N:21]([CH2:14][C@H:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][C@H:10]1[OH:20])=[N+:22]=[N-:23]

참가 물질

6

반응물 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86753635cis-l-Tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidine

생성물 1

HCID 86657830cis-4-Azidomethyl-1-tert-butoxycarbonyl-3-hydroxypiperidine수율 92.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To a solution of cis-1-tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidine (4.44 g) in dimethylformamide (60 ml) were added sodium azide (1.4 g) and ammonium chloride (1.15 g), and the resulting mixture was stirred at 60° C. for 6 hr. Water was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with brine and dried. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=40:1) to give 3.4 g of cis-4-azidomethyl-1-tert-butoxycarbonyl-3-hydroxypiperidine.

후처리

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with brine
  3. customdried
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol=40:1)

출처 및 근거

ORD 기록
ord-97df34546f294ddb8456e8f561dab525
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05864039

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