Potassium tert-butoxide → 3-(5-Bromo-4-fluoro-2-methyl-phenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one

HRID 1962376ノート

反応式

HRID 1962376 の反応式
CO[C:3]([C:5]1([NH:13][C:14](=[O:25])[CH2:15][C:16]2[CH:21]=[C:20]([Br:22])[C:19]([F:23])=[CH:18][C:17]=2[CH3:24])[CH2:10][CH2:9][N:8]([O:11][CH3:12])[CH2:7][CH2:6]1)=[O:4].CC(C)([O-])C.[K+]>CN(C)C=O>[Br:22][C:20]1[C:19]([F:23])=[CH:18][C:17]([CH3:24])=[C:16]([C:15]2[C:14](=[O:25])[NH:13][C:5]3([CH2:10][CH2:9][N:8]([O:11][CH3:12])[CH2:7][CH2:6]3)[C:3]=2[OH:4])[CH:21]=1

参加物

4

反応物 2

HCID 23665647Potassium tert-butoxideHCID 596145984-[2-(5-Bromo-4-fluoro-2-methyl-phenyl)-acetylamino]-1-methoxy-piperidine-4-carboxylic acid methyl ester

生成物 1

HCID 596145973-(5-Bromo-4-fluoro-2-methyl-phenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-[2-(5-bromo-4-fluoro-2-methyl-phenyl)-acetylamino]-1-methoxy-piperidine-4-carboxylic acid methyl ester (6.0 g) in dimethylformamide (20 ml) at 100° C. was added potassium tert-butoxide (3.23 g) and stirring continued at 100° C. for 10 minutes. The reaction mixture was quenched at room temperature by addition of acetic acid (1.64 ml), diluted with water (20 ml) and extracted with tert-butyl methyl ether (3×). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was triturated with acetonitrile, filtered and dried. Yield: 3.69 g of 3-(5-bromo-4-fluoro-2-methyl-phenyl)-4-hydroxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one (title compound C19) as a solid, mp: 229-230° C.

後処理

  1. customThe reaction mixture was quenched at room temperature by addition of acetic acid (1.64 ml)
  2. additiondiluted with water (20 ml)
  3. extractionextracted with tert-butyl methyl ether (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was triturated with acetonitrile
  8. filtrationfiltered
  9. customdried

出典と根拠

ORDレコード
ord-efd8fa4acb224f978d0dfd6bff44acba
出典データセット
uspto-grants-2013_04
特許番号
US08415369B2

反応ノート

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