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 1662474ノート

反応式

HRID 1662474 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-366654af05f644e59206834295c4caf3
出典データセット
uspto-grants-2011_10
特許番号
US08030354B2

反応ノート

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