4'-[3-(3-Oxo-1-pyrrolidinyl)propoxy][1,1'-biphenyl]-4-carbonitrile → 4'-[3-(3-Hydroxy-3-isopropyl-1-pyrrolidinyl)propoxy][1,1'-biphenyl]-4-carbonitrile

HRID 1167845노트

반응식

HRID 1167845 반응식
[O:1]=[C:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:3]1.[CH:25]([Mg]Cl)([CH3:27])[CH3:26]>C1COCC1>[OH:1][C:2]1([CH:25]([CH3:27])[CH3:26])[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:18]=[CH:19][C:20]([C:23]#[N:24])=[CH:21][CH:22]=3)=[CH:13][CH:12]=2)[CH2:3]1

참가 물질

4

반응물 2

HCID 99230964'-[3-(3-Oxo-1-pyrrolidinyl)propoxy][1,1'-biphenyl]-4-carbonitrileHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 102922444'-[3-(3-Hydroxy-3-isopropyl-1-pyrrolidinyl)propoxy][1,1'-biphenyl]-4-carbonitrile수율 75%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The product from Example 154 (147 mg, 0.46 mmol) in dry THF (10 mL) under an atmosphere of nitrogen at 0° C. was treated with a 2.0M solution of isopropylmagnesium chloride (0.92 mmol). After warming to ambient temperature and stirring for 1 hour, the mixture was quenched with 5 mL of cold saturated ammonium chloride solution and then the solution was partitioned between water (50 mL) and dichloromethane (50 mL). The organic layer was washed with brine (50 mL), dried over sodium sulfate and filtered. The filtrate was evaporated under reduced pressure and the residue purified by chromatography (CHCl3:MeOH:NH4OH, 9:1:0.1) to provide the title compound (75% yield).

후처리

  1. customthe mixture was quenched with 5 mL of cold saturated ammonium chloride solution
  2. customthe solution was partitioned between water (50 mL) and dichloromethane (50 mL)
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customthe residue purified by chromatography (CHCl3:MeOH:NH4OH, 9:1:0.1)

출처 및 근거

ORD 기록
ord-582b98ef7a8c48b7a650403d134dbce3
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06620839B2

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