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 1022388ノート

反応式

HRID 1022388 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. is added potassium tert-butoxide (3.23 g) and stirring continued at 100° C. for 10 minutes. The reaction mixture is 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 are washed with brine, dried over sodium sulfate and concentrated. The residue is 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 as a solid, mp: 229-230° C.

後処理

  1. customThe reaction mixture is 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 are washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is triturated with acetonitrile
  8. filtrationfiltered
  9. customdried

出典と根拠

ORDレコード
ord-0f8ae5b9e44a4ed380eb39dbf4be8a53
出典データセット
uspto-grants-2014_05
特許番号
US08722578B2

反応ノート

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