1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 4-[(1R)-1-azidoethyl]benzoate

HRID 1431996노트

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HRID 1431996 반응식
O[C@H:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)[CH3:3].C1C=CC(P([N:28]=[N+:29]=[N-:30])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.CCOC(C)=O>[N:28]([C@@H:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)[CH3:3])=[N+:29]=[N-:30]

참가 물질

6

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 6932348methyl 4-((1S)-1-hydroxyethyl)benzoate

생성물 1

HCID 16108955Methyl 4-[(1R)-1-azidoethyl]benzoate

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of (S)-methyl 4-(1-hydroxyethyl)benzoate (24.8 g, 138 mmol) in toluene (300 mL) was cooled in ice-salt bath (bath temp: −10° C.). DPPA (36.3 mL, 168 mmol) was then added dropwise over 15 min (Bath temp was kept at −10° C. during addition). After 5 min, DBU (25.3 mL, 169 mmol) was added over 8 min. The ice in the bath was allowed to melt and the reaction mixture was stirred overnight at RT. The reaction mixture was diluted with EtOAc (200 mL), and washed with 0.1 N HCl aq. (300 mL). The aqueous layer was extracted with EtOAc (100 mL×2) and the combined organic phase was further washed with 0.1N HCl aq. (300 mL×2), 5% NaHCO3 (300 mL×2), and saturated NaCl (300 mL×2). The organic layers was dried over Na2SO4 and concentrated under reduced pressure. The crude product was chromatographed on SiO2 (ISCO: hexane/CH2Cl2=3/1→3/7) to yield the title compound. MS (m/z): 206.2 (m+H).

후처리

  1. addition(Bath temp was kept at −10° C. during addition)
  2. washwashed with 0.1 N HCl aq. (300 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (100 mL×2)
  4. washthe combined organic phase was further washed with 0.1N HCl aq. (300 mL×2), 5% NaHCO3 (300 mL×2), and saturated NaCl (300 mL×2)
  5. dry with materialThe organic layers was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was chromatographed on SiO2 (ISCO: hexane/CH2Cl2=3/1→3/7)

출처 및 근거

ORD 기록
ord-bb59237093e3434ead6ba4d5225ff40b
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612060B2

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