ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Methyl iodide → 10-{4-[(3R)-3-Methoxy-2-methylcyclohex-1-en-1-yl]-3-methylbenzoyl}-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

HRID 1794023
ノート
印刷プレビュー

反応式

HRID 1794023 の反応式
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH2:28][CH2:27][CH2:26][C@@H:25]([OH:29])[C:24]=4[CH3:30])=[C:19]([CH3:31])[CH:18]=3)=[O:16])[CH2:6][C:5]=12.[H-].[Na+].[H][H].[CH3:36]I>O1CCCC1>[CH3:36][O:29][C@@H:25]1[CH2:26][CH2:27][CH2:28][C:23]([C:20]2[CH:21]=[CH:22][C:17]([C:15]([N:7]3[C:8]4[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=4[CH2:10][N:4]4[CH:3]=[CH:2][CH:1]=[C:5]4[CH2:6]3)=[O:16])=[CH:18][C:19]=2[CH3:31])=[C:24]1[CH3:30]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 24758Sodium hydride2 回HCID 69313729(10, 11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[4-((3R)-3-hydroxy-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-methanoneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 6965259710-{4-[(3R)-3-Methoxy-2-methylcyclohex-1-en-1-yl]-3-methylbenzoyl}-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine
収率 92.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[4-((3R)-3-hydroxy-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-methanone of Example 41 (0.125 g, 0.303 mmol) was dissolved in anhydrous tetrahydrofuran (3.0 mL) followed by addition of sodium hydride (0.008 g, 0.333 mmol). After hydrogen gas evolution ceased (5 minutes), methyl iodide (0.038 mL, 0.606 mmol) was added and the reaction stirred for 30 minutes. Additional sodium hydride (0.008 g, 0.333 mmol) was added and stirring continued overnight. The reaction was quenched with saturated ammonium chloride (50 mL) and extracted with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated. Purification of the residue by flash column chromatography, eluting with 30% ethyl acetate in hexane, followed by recrystallization from petroleum ether afforded the title compound (0.120 g) as white crystals, m.p. 127–128° C.; [α]D=+45.65 (c=1.0, chloroform). Single crystal X-ray crystallography established the absolute configuration as the (R)-isomer.

後処理

  1. additionwas added
  2. stirringstirring continued overnight
  3. customThe reaction was quenched with saturated ammonium chloride (50 mL)
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue by flash column chromatography
  9. washeluting with 30% ethyl acetate in hexane
  10. customfollowed by recrystallization from petroleum ether

出典と根拠

ORDレコード
ord-ee7db355ab6d4314a6a982eb170a2214
出典データセット
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07022699B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート