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

HRID 1162053노트

반응식

HRID 1162053 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 935Nickel촉매HCID 21873804Tetrahydrofuran ethanol용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-f0df95dfdccc46af8b9e442cab6e37f9
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820675B2

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