2,5-Dimethylpyrrolidine, (2R,5R)- → Methyl 2-(((2R,5R)-2,5-dimethyl-1-pyrrolidinyl)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662474노트

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HRID 1662474 반응식
C([BH3-])#N.[Na+].[F:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][C:15]=1[CH:24]=O.[CH3:26][C@@H:27]1[CH2:31][CH2:30][C@@H:29]([CH3:32])[NH:28]1>CO.CCOC(C)=O>[CH3:26][C@@H:27]1[CH2:31][CH2:30][C@@H:29]([CH3:32])[N:28]1[CH2:24][C:15]1[CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=[CH:19][C:14]=1[C:7]1[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=[CH:11][C:6]=1[F:5]

참가 물질

6

반응물 3

HCID 6417672,5-Dimethylpyrrolidine, (2R,5R)-HCID 5003444Sodium cyanoborohydrideHCID 574676302'-Fluoro-2-formyl-5'-methoxy-biphenyl-4-carboxylic acid methyl ester

생성물 1

HCID 57705891Methyl 2-(((2R,5R)-2,5-dimethyl-1-pyrrolidinyl)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate수율 13.9%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

Sodium cyanoborohydride (0.071 g, 1.1 mmol) was added to a solution of 66.60C (0.180 g, 0.62 mmol) and (2R,5R)-2,5-dimethylpyrrolidine (available from Aldrich) (0.073 g, 0.74 mmol) in MeOH (3 mL). The reaction was stirred at 110° C. for 30 minutes and then was diluted with EtOAc (100 mL). The mixture was washed with an aqueous Na2CO3 solution and brine, and dried over anhydrous sodium sulfate. After filtration, solvent was removed, and the residue was purified by flash chromatography (silica gel, 1:6 EtOAc/hexane) and gave 66.71A (32 mg).

후처리

  1. washThe mixture was washed with an aqueous Na2CO3 solution and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationAfter filtration, solvent
  4. customwas removed
  5. customthe residue was purified by flash chromatography (silica gel, 1:6 EtOAc/hexane)

출처 및 근거

ORD 기록
ord-366654af05f644e59206834295c4caf3
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030354B2

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