1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-[(1S)-1-azidoethyl]-5-bromopyridine

HRID 1255840

반응식

HRID 1255840 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C@H:8](O)[CH3:9])[CH:5]=[N:6][CH:7]=1.C1(P([N:25]=[N+:26]=[N-:27])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>O1CCCC1.C(OCC)(=O)C.O>[N:25]([C@H:8]([C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[CH3:9])=[N+:26]=[N-:27]

참가 물질

7

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 68655864(R)-1-(5-bromopyridin-3-yl)ethanol

생성물 1

HCID 866418603-[(1S)-1-azidoethyl]-5-bromopyridine수율 75%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (1R)-1-(5-bromopyridin-3-yl)ethanol (10 mmol) in tetrahydrofuran (40 mL), cooled to 0° C., was added diphenylphosphoryl azide (4.3 mL, 20 mmol) in one portion followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (3 mL, 20 mmol) dropwise over 30 minutes. After this time the reaction mixture was allowed to warm slowly to room temperature and was stirred overnight. The mixture was diluted with ethyl acetate (50 mL) and water (50 mL), the two phases separated and the aqueous phase extracted with ethyl acetate (3×50 mL). The combined organic phases were washed with brine (50 mL), dried (MgSO4) and concentrated under reduced pressure to give a black liquid which was purified by flash chromatography (silica, ethyl acetate/hexanes) to give 3-[(1S)-1-azidoethyl]-5-bromopyridine (1.7 g, 75%) as a colourless liquid.

후처리

  1. customthe two phases separated
  2. extractionthe aqueous phase extracted with ethyl acetate (3×50 mL)
  3. washThe combined organic phases were washed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give a black liquid which
  7. customwas purified by flash chromatography (silica, ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-4db8b242fd664bfd922465040967c31a
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461161B2

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