Hydrazine hydrate (1:1) → Tert-butyl 4-[(5-amino-1-benzofuran-7-yl)methyl]-3-methylpiperazine-1-carboxylate

HRID 1162053ノート

反応式

HRID 1162053 の反応式
O.NN.[CH3:4][CH:5]1[N:10]([CH2:11][C:12]2[C:20]3[O:19][CH:18]=[CH:17][C:16]=3[CH:15]=[C:14]([N+:21]([O-])=O)[CH:13]=2)[CH2:9][CH2:8][N:7]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:6]1>[Ni].C(O)C.C1COCC1>[NH2:21][C:14]1[CH:13]=[C:12]([CH2:11][N:10]2[CH2:9][CH2:8][N:7]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:6][CH:5]2[CH3:4])[C:20]2[O:19][CH:18]=[CH:17][C:16]=2[CH:15]=1

参加物

5

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 66893976Tert-butyl 3-methyl-4-[(5-nitro-1-benzofuran-7-yl)methyl]piperazine-1-carboxylate

生成物 1

HCID 66892829Tert-butyl 4-[(5-amino-1-benzofuran-7-yl)methyl]-3-methylpiperazine-1-carboxylate収率 127%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 21873804Tetrahydrofuran ethanol溶媒

実験手順

Raney nickel (slurry in ethanol) and hydrazine hydrate (97 μL, 2.0 mmol) were added to tert-butyl 3-methyl-4-[(5-nitro-1-benzofuran-7-yl)methyl]piperazine-1-carboxylate (115 mg, 0.31 mmol; obtained in Step 1) in ethanol:THF (4:1; 5 mL). The resulting mixture was stirred at room temperature for 1.5 h, followed by filtration through Celite. The Celite pad was rinsed several times with ethanol. The solvent was evaporated to give the crude product (136 mg) as a light green solid. This material was used in the next step without further purification. HPLC 98%, RT=1.77 min (System A; 5-60% MeCN over 3 min), 100%, RT=1.50 min (System B; 5-60% MeCN over 3 min). MS (ESI+) for C19H27N3O3 m/z 346 (M+H)+.

後処理

  1. filtrationfollowed by filtration through Celite
  2. washThe Celite pad was rinsed several times with ethanol
  3. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-f0df95dfdccc46af8b9e442cab6e37f9
出典データセット
uspto-grants-2010_10
特許番号
US07820675B2

反応ノート

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