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Potassium hydride → (E)-3-[4-((S)-1-{2-[3,5-dimethyl-1-(tetrahydropyran-4-ylmethyl)-1H-pyrazol-4-yl]-ethyl}-pyrrolidin-2-yl)-phenyl]-acrylic acid methyl ester

HRID 1802796
ノート
印刷プレビュー

反応式

HRID 1802796 の反応式
[CH3:1][O:2][C:3](=[O:26])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:17][CH2:18][C:19]2[C:20]([CH3:25])=[N:21][NH:22][C:23]=2[CH3:24])=[CH:8][CH:7]=1.[H-].[K+].Br[CH2:30][CH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>O1CCCC1.CS(C)=O>[CH3:1][O:2][C:3](=[O:26])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]([C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:17][CH2:18][C:19]2[C:20]([CH3:25])=[N:21][N:22]([CH2:30][CH:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[C:23]=2[CH3:24])=[CH:10][CH:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 82127Potassium hydrideHCID 27732864-(Bromomethyl)oxaneHCID 57899243(E)-3-(4-{(S)-1-[2-(3,5-dimethyl-1H-pyrazol-4-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester

生成物 1

HCID 57899315(E)-3-[4-((S)-1-{2-[3,5-dimethyl-1-(tetrahydropyran-4-ylmethyl)-1H-pyrazol-4-yl]-ethyl}-pyrrolidin-2-yl)-phenyl]-acrylic acid methyl ester収率 14.6%

試薬・触媒・溶媒 1

HCID 21830753
dimethylsulfoxide THF
溶媒

実験手順

To an ice cold mixture of (E)-3-(4-{(S)-1-[2-(3,5-dimethyl-1H-pyrazol-4-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester (0.85 g, 2.4 mmol) and potassium hydride (115 mg, 2.88 mmol) in 4.0 mL tetrahydrofuran:dimethyl sulfoxide (9:1 v/v) was added 4-bromomethyltetrahydropyran (945 mg, 5.28 mmol). The mixture was slowly warmed to room temperature and stirred under nitrogen for 16 h. It was then quenched with aqueous ammonium chloride and added with ethyl acetate. The layers were separated and the organic layer was washed with more aqueous ammonium chloride. The aqueous layers were then washed with more ethyl acetate and the combined organic extracts were dried over magnesium sulfate and concentrated to a yellow oil. The oil was then purified via silica gel column chromatography (100:0 to 0:100 heptane:ethyl acetate) to give (E)-3-[4-((S)-1-{2-[3,5-dimethyl-1-(tetrahydropyran-4-ylmethyl)-1H-pyrazol-4-yl]-ethyl}-pyrrolidin-2-yl)-phenyl]-acrylic acid methyl ester (160 mg, 0.35 mmol, 14% yield) as a yellow oil. LC/MS (m/z): 452.5 (M+1).

後処理

  1. customIt was then quenched with aqueous ammonium chloride
  2. additionadded with ethyl acetate
  3. customThe layers were separated
  4. washthe organic layer was washed with more aqueous ammonium chloride
  5. washThe aqueous layers were then washed with more ethyl acetate
  6. dry with materialthe combined organic extracts were dried over magnesium sulfate
  7. concentrationconcentrated to a yellow oil
  8. customThe oil was then purified via silica gel column chromatography (100:0 to 0:100 heptane:ethyl acetate)

出典と根拠

ORDレコード
ord-46e6abb9b5cc4a78be152b5c8b663558
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08349883B2

反応ノート

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