1,8-Diazabicyclo(5.4.0)undec-7-ene → (R)-1-azido-5-bromo-indane

HRID 1913402노트

반응식

HRID 1913402 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C@@H:7](O)[CH2:6][CH2:5]2.C1C=CC(OP(OC2C=CC=CC=2)([N:21]=[N+:22]=[N-:23])=O)=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.CCOC(C)=O>[N:21]([C@H:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1)=[N+:22]=[N-:23]

참가 물질

6

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123414Diphenylphosphoryl azideHCID 29414737(1S)-5-bromo-2,3-dihydro-1H-inden-1-ol

생성물 1

HCID 59179602(R)-1-azido-5-bromo-indane수율 83.5%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
15 °C

실험 절차

A solution of (S)-5-bromo-indan-1-ol (15.0 g, 70.4 mmol) in toluene (150 mL) was cooled in an ice bath under N2 and was treated with diphenylphosphoric azide (DPPA, 22.0 g, 91.5 mmol) in one portion followed by 1,8-diazabicyclo[5,4,0]undec-7-ene (15.0 g, 98.6 mmol). The reaction temperature was kept between 3 and 10° C. during 3 hours of addition and the mixture was warmed to 15° C. over the next hour (TLC indicated no starting material). The mixture was diluted with EtOAc (300 mL) and was washed with water. The organic layer was dried over Na2SO4, filtered and concentrated to give a dark oil. The crude product was purified by silica gel column (packed with 1% Et3N in hexanes, hexane eluant) to give (R)-1-azido-5-bromo-indane (14 g, 83%) as an oil which was used directly in the next step.

후처리

  1. additionThe reaction temperature was kept between 3 and 10° C. during 3 hours of addition
  2. washwas washed with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a dark oil
  7. customThe crude product was purified by silica gel column (packed with 1% Et3N in hexanes, hexane eluant)

출처 및 근거

ORD 기록
ord-72eacf37d2454f4ba447640a285f3583
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609680B2

반응 노트

불러오는 중…