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3-Iodotoluene → Rac-4-phenyl-8-(1-m-tolyl-cyclohexyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 914937
ノート
印刷プレビュー

反応式

HRID 914937 の反応式
I[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=C[CH:7]=1.C([Mg]Cl)(C)C.[O:14]=[C:15]1[C:19]2([CH2:24][CH2:23][N:22]([C:25]3([C:31]#N)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH2:21][CH2:20]2)[CH:18]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:17][NH:16]1>C1COCC1>[C:33]1([CH:18]2[C:19]3([CH2:24][CH2:23][N:22]([C:25]4([C:31]5[CH:5]=[C:4]([CH3:8])[CH:3]=[CH:2][CH:7]=5)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]4)[CH2:21][CH2:20]3)[C:15](=[O:14])[NH:16][CH2:17]2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=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

5

反応物 3

HCID 122683-IodotolueneHCID 69486548Rac-1-(1-oxo-4-phenyl-2,8-diaza-spiro [4.5]dec-8-yl)-cyclohexanecarbonitrileHCID 178418918HCID 178418918、化合物

生成物 1

HCID 11373041Rac-4-phenyl-8-(1-m-tolyl-cyclohexyl)-2,8-diaza-spiro[4.5]decan-1-one収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 3-iodotoluene (388 mg, 1.8 mmol) in dry THF (6 mL) under argon at -60° C. was added isopropylmagnesium chloride (2 M solution in THF, 977 μL, 2.0 mmol) and the resulting solution allowed to warm up to 0° C. over 1 h and then to room temperature over 10 min. The resulting solution was then added dropwise to a solution of rac-1-(1-oxo-4-phenyl-2,8-diaza-spiro[4.5]dec-8-yl)-cyclohexanecarbonitrile (200 mg, 0.6 mmol) in dry THF (3 mL) and the solution stirred overnight at room temperature. The reaction was quenched by the addition of ammonium chloride solution (sat., 10 mL) and the product extracted with ethyl acetate (2×20 mL). The combined organic extracts were then washed with brine (20 mL), dried over sodium sulfate, filtered and evaporated. The residue was purified by chromatography on silica gel eluting with DCM:MeOH:NH4OH (95:4.5:0.5) to afford the title compound (170 mg, 71%) as a white solid. MS: m/e=403.6 (M+H).

後処理

  1. customThe reaction was quenched by the addition of ammonium chloride solution (sat., 10 mL)
  2. extractionthe product extracted with ethyl acetate (2×20 mL)
  3. washThe combined organic extracts were then washed with brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel eluting with DCM:MeOH:NH4OH (95:4.5:0.5)

出典と根拠

ORDレコード
ord-92db3e2d0d5d4ccc98a7ef3095417625
出典データセット
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07265126B2

反応ノート

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