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Sodium hydride → (3aRS,4RS,6aSR)-4-[4-(amino-hydroxyimino-methyl)-benzyl]-2-benzyl-5,6,6-trimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione

HRID 2293302
ノート
印刷プレビュー

反応式

HRID 2293302 の反応式
Cl.[NH2:2][OH:3].[H-].[Na+].[CH2:6]([N:13]1[C:17](=[O:18])[CH:16]2[C:19]([CH3:33])([CH3:32])[N:20]([CH3:31])[CH:21]([CH2:22][C:23]3[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=3)[CH:15]2[C:14]1=[O:34])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CN(C=O)C>[NH2:28][C:27](=[N:2][OH:3])[C:26]1[CH:25]=[CH:24][C:23]([CH2:22][CH:21]2[N:20]([CH3:31])[C:19]([CH3:32])([CH3:33])[CH:16]3[C:17](=[O:18])[N:13]([CH2:6][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:14](=[O:34])[CH:15]23)=[CH:30][CH:29]=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 24758Sodium hydrideHCID 443297Hydroxyamine hydrochlorideHCID 69954349(1RS,3aSR,6aRS)-4-(5-benzyl-2,3,3-trimethyl-4,6-dioxo-octahydro-pyrrolo[3,4-c]pyrrol-1-ylmethyl)-benzonitrile

生成物 1

HCID 86751566(3aRS,4RS,6aSR)-4-[4-(amino-hydroxyimino-methyl)-benzyl]-2-benzyl-5,6,6-trimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione収率 97.7%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒
2 回

反応条件

温度
0 °C

実験手順

2.19 g (31.56 mmol) of hydroxylamine hydrochloride were suspended in 8 ml of DMF and cooled to 0° C. 0.79 g (26.3 mmol) of 80% sodium hydride was added slowly. 1.02 g (2.63 mmol) of (1RS, 3aSR,6aRS)-4-(5-benzyl-2,3,3-trimethyl-4,6-dioxo-octahydro-pyrrolo[3,4-c]pyrrol-1-ylmethyl)-benzonitrile were dissolved in DMF and added to the reaction mixture. The cooling was then no longer applied. The mixture was stirred at room temperature for 2 days. Thereafter, it was filtered and the DMF was removed in a high vacuum. The mixture was purified chromatographically (RP18, gradient from water to methanol). 1.08 g (97%) of (3aRS,4RS,6aSR)-4-[4-(amino-hydroxyimino-methyl)-benzyl]-2-benzyl-5,6,6-trimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione were isolated as a colourless powder. M.p.: 189°-192° C. ISP-MS: 421.5 ([M+H]+, 100).

後処理

  1. additionadded to the reaction mixture
  2. filtrationThereafter, it was filtered
  3. customthe DMF was removed in a high vacuum
  4. customThe mixture was purified chromatographically (RP18, gradient from water to methanol)

出典と根拠

ORDレコード
ord-ba980332df26429d9a45ea4cb65ea0be
出典データセット
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05686459

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