Ethyl formate → 7-(3-Bromophenyl)-2-(hydroxymethylene)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one

HRID 2061614노트

반응식

HRID 2061614 반응식
[CH3:1][CH2:2][O-:3].[Na+].[Br:5][C:6]1[CH:7]=[C:8]([CH:12]2[CH2:19][CH:18]3[N:20]([S:21]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)(=[O:23])=[O:22])[CH:14](C[C:16](=[O:34])[CH2:17]3)[CH2:13]2)[CH:9]=[CH:10][CH:11]=1.C(OCC)=O>C1COCC1.[NH4+].[Cl-]>[Br:5][C:6]1[CH:7]=[C:8]([CH:12]2[CH2:13][CH:14]3[N:20]([S:21]([C:24]4[CH:25]=[CH:26][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:28][CH:29]=4)(=[O:23])=[O:22])[CH:18]([CH2:17][C:16](=[O:34])[C:1]3=[CH:2][OH:3])[CH2:19]2)[CH:9]=[CH:10][CH:11]=1

참가 물질

6

반응물 3

HCID 8025Ethyl formateHCID 2723922Sodium ethoxideHCID 673032167-(3-Bromophenyl)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one

생성물 1

HCID 673031627-(3-Bromophenyl)-2-(hydroxymethylene)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 25517Ammonium Chloride용매

실험 절차

21% NaOEt (6 ml, 16.1 mmol) was added to a solution of 7-(3-Bromophenyl)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one (90) (2.28 g, 4.54 mmol) and ethyl formate (6 ml, 74.5 mmol) in THF (20 ml). The solution was placed into a preheated oil bath at 60° C. After stirring for 30 min, the solution was cooled to ambient temperature, diluted with saturated aqueous NH4Cl, and extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered, and concentrated to afford 7-(3-bromophenyl)-2-(hydroxymethylene)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one. Hydrazine monohydrate (3 ml) was added to a solution of 7-(3-bromophenyl)-2-(hydroxymethylene)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one and glacial acetic acid (1 ml) in EtOH (20 ml). After stirring for 18 h, the solution was concentrated to afford compound 92.

후처리

  1. customThe solution was placed into a preheated oil bath at 60° C
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-af228f87e7af4796ab62ba7b5be9323f
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283358B2

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