Sodium hydride → [(2R)-4-methylmorpholin-2-yl]methyl 4-phenylpiperazine-1-carboxylate

HRID 2262492ノート

反応式

HRID 2262492 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][O:5][C@@H:4]([CH2:8][OH:9])[CH2:3]1.[H-].[Na+].[C:12]1([N:18]2[CH2:23][CH2:22][N:21]([C:24](OC3C=CC([N+]([O-])=O)=CC=3)=[O:25])[CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[C:12]1([N:18]2[CH2:19][CH2:20][N:21]([C:24]([O:9][CH2:8][C@@H:4]3[O:5][CH2:6][CH2:7][N:2]([CH3:1])[CH2:3]3)=[O:25])[CH2:22][CH2:23]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 40152301(R)-4-Methyl-2-(hydroxymethyl)morpholine2 回HCID 595944814-Nitrophenyl 4-phenylpiperazine-1-carboxylate2 回

生成物 1

HCID 42634004[(2R)-4-methylmorpholin-2-yl]methyl 4-phenylpiperazine-1-carboxylate収率 72.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(R)-(4-Methyl-morpholin-2-yl)-methanol (Intermediate 11; 100 mg, 0.76 mmol) was added to a suspension of NaH (60% dispersion in oil; 90.0 mg, 2.28 mmol) in anhydrous THF (7 mL) and stirred under nitrogen for 30 min. 4-Nitrophenyl 4-phenylpiperazine-1-carboxylate (Intermediate 2; 300 mg, 0.92 mmol) was added and the reaction mixture was stirred at room temperature for 48 h. The reaction mixture was filtered through celite and the solid washed with THF (10 mL). The filtrates were combined and the solvent removed in vacuo. The residue was purified by column chromatography (normal phase silica, 5 g Isolute-Si column, gradient 1-5% MeOH in DCM). The solvents were removed in vacuo to give [(2R)-4-methylmorpholin-2-yl]methyl 4-phenylpiperazine-1-carboxylate (175 mg, 72%) as a light yellow gum

後処理

  1. stirringthe reaction mixture was stirred at room temperature for 48 h
  2. filtrationThe reaction mixture was filtered through celite
  3. washthe solid washed with THF (10 mL)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by column chromatography (normal phase silica, 5 g Isolute-Si column, gradient 1-5% MeOH in DCM)
  6. customThe solvents were removed in vacuo

出典と根拠

ORDレコード
ord-43b6062746024278ab38a42e7d8a61cb
出典データセット
uspto-grants-2010_12
特許番号
US07851471B2

反応ノート

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