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Lithium borohydride → 4-[(6-Chloro-2-naphthyl)sulfonyl]-6-(hydoxymethyl)-1-[methyl[1-(4-pyridinyl)-4-piperidinyl]amino]-2-piperazinone hydrochloride

HRID 2086304
ノート
印刷プレビュー

反応式

HRID 2086304 の反応式
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][C:20](=[O:22])[N:19]([N:23]([CH3:36])[CH:24]3[CH2:29][CH2:28][N:27]([C:30]4[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=4)[CH2:26][CH2:25]3)[CH:18]([C:37](OC)=[O:38])[CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2.[BH4-].[Li+].Cl.CO>CO>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:17][CH:18]([CH2:37][OH:38])[N:19]([N:23]([CH3:36])[CH:24]3[CH2:25][CH2:26][N:27]([C:30]4[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=4)[CH2:28][CH2:29]3)[C:20](=[O:22])[CH2:21]1)(=[O:14])=[O:15])[CH:7]=[CH:6]2
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 4148881Lithium borohydrideHCID 21893726Hydrochloride methanolHCID 22727077Methyl 4-[(6-chloro-2-naphthyl)sulfonyl)-1-[methyl[1-(4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazinecarboxylate hydrochloride

生成物 1

HCID 227272524-[(6-Chloro-2-naphthyl)sulfonyl]-6-(hydoxymethyl)-1-[methyl[1-(4-pyridinyl)-4-piperidinyl]amino]-2-piperazinone hydrochloride収率 83.9%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

反応条件

温度
0 °C

実験手順

A solution of methyl 4-[(6-chloro-2-naphthyl)sulfonyl)-1-[methyl[1-(4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazinecarboxylate hydrochloride (0.3 g) in methanol (20 ml) was treated with 3 portions of lithium borohydride (1.14 g) with stirring at 0° C. After completion of the reaction, the reaction system was adjusted at pH 4 with a 10% hydrochloric acid/methanol solution, and then concentrated under reduced pressure. The residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate, and the organic phase was dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified on a CHP-20 column (water→1% 1N hydrochloric acid-containing 30% aqueous solution of acetonitrile) to obtain the title compound (0.12 g) as a colorless powder.

後処理

  1. customAfter completion of the reaction
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified on a CHP-20 column (water→1% 1N hydrochloric acid-containing 30% aqueous solution of acetonitrile)

出典と根拠

ORDレコード
ord-988f8499adfc4b728093ef425ac0f44e
出典データセット
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06723722B1

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート