1,8-Diazabicyclo(5.4.0)undec-7-ene → 4(R)-Azido-6,8-dibromo-chroman

HRID 1008959노트

반응식

HRID 1008959 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Br:12])[CH:11]=1)[O:8][CH2:7][CH2:6][C@@H:5]2O.C1(P([N:28]=[N+:29]=[N-:30])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>O1CCCC1.C(OC(=O)C)C>[N:28]([C@H:5]1[C:4]2[C:9](=[C:10]([Br:12])[CH:11]=[C:2]([Br:1])[CH:3]=2)[O:8][CH2:7][CH2:6]1)=[N+:29]=[N-:30]

참가 물질

6

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 67304261(S)-6,8-Dibromochroman-4-ol

생성물 1

HCID 866200164(R)-Azido-6,8-dibromo-chroman

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution containing 6,8-dibromo-chroman-4(S)-ol in tetrahydrofuran (0.17M) and 1.2 equivalents of diphenylphosphorylazide was stirred for 15 minutes at room temperature. The solution was cooled to 10° C. and 2.5 equivalents of 1,8-diazabicyclo[5.4.0]undec-7-ene added. The mixture was stirred with gradual warming to room temperature and maintained for 48 h. The mixture was diluted with ethylacetate and washed with brine followed by water. The organic phase was concentrated to afford the title compound as a tan oil.

후처리

  1. temperatureThe solution was cooled to 10° C.
  2. stirringThe mixture was stirred
  3. temperaturewith gradual warming to room temperature
  4. temperaturemaintained for 48 h
  5. washwashed with brine
  6. concentrationThe organic phase was concentrated

출처 및 근거

ORD 기록
ord-a7dbc9ef49184c28889d6fa51a957303
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973050B2

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