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Benzyl Alcohol → 8-(2-Benzyloxy-pyridine-3-sulfonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 2194176
ノート
印刷プレビュー

反応式

HRID 2194176 の反応式
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:12]1[C:17]([S:18]([N:21]2[CH2:42][CH2:41][C:24]3([C:28](=[O:29])[N:27]([C:30]4[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=4)[CH2:26][CH2:25]3)[CH2:23][CH2:22]2)(=[O:20])=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:3]([O:10][C:12]1[C:17]([S:18]([N:21]2[CH2:22][CH2:23][C:24]3([C:28](=[O:29])[N:27]([C:30]4[CH:31]=[CH:32][C:33]([O:36][C:37]([F:38])([F:39])[F:40])=[CH:34][CH:35]=4)[CH2:26][CH2:25]3)[CH2:41][CH2:42]2)(=[O:20])=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 595779608-(2-Chloro-pyridine-3-sulfonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

生成物 1

HCID 667872738-(2-Benzyloxy-pyridine-3-sulfonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one収率 89%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
2 回
HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a suspension of NaH (12 mg, 0.31 mmol) in DMF (2 mL) at 0° C. was added benzyl alcohol (25 uL, 0.25 mmol) and the mixture was stirred for 30 min at 0° C. A solution of 8-(2-chloro-pyridine-3-sulfonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one (described in example 188, 100 mg, 0.20 mmol) in DMF (500 uL) was added drop-wise and the reaction mixture was allowed to warm to room temperature and stirred for 16 h. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo to give the crude residue which was purified by flash column chromatography (1:2 AcOEt/heptane) which afforded the desired product as a colourless solid (100 mg, 87%). MS (ESI): 562.3 (MH+).

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred for 16 h
  3. washwashed with brine
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the crude residue which
  8. customwas purified by flash column chromatography (1:2 AcOEt/heptane) which

出典と根拠

ORDレコード
ord-d6f9e6e7b35847b49701834aca5fc2e4
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08329904B2

反応ノート

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