Hydrazine hydrate (1:1) → 1,1-Dimethylethyl 4-({2-amino-5-methyl-4-[(1-methylethyl)oxy]phenyl}amino)-1-piperidinecarboxylate

HRID 2064179ノート

反応式

HRID 2064179 の反応式
[CH3:1][C:2]1[C:3]([O:25][CH:26]([CH3:28])[CH3:27])=[CH:4][C:5]([N+:22]([O-])=O)=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:7]=1.O.NN>C(O)C.[Ni]>[NH2:22][C:5]1[CH:4]=[C:3]([O:25][CH:26]([CH3:27])[CH3:28])[C:2]([CH3:1])=[CH:7][C:6]=1[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:11][CH2:10]1

参加物

5

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 598501711,1-Dimethylethyl 4-({5-methyl-4-[(1-methylethyl)oxy]-2-nitrophenyl}amino)-1-piperidinecarboxylate

生成物 1

HCID 598501841,1-Dimethylethyl 4-({2-amino-5-methyl-4-[(1-methylethyl)oxy]phenyl}amino)-1-piperidinecarboxylate収率 83%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒

反応条件

温度
45 °C

実験手順

A suspension/solution of 1,1-dimethylethyl 4-({5-methyl-4-[(1-methylethyl)oxy]-2-nitrophenyl}amino)-1-piperidinecarboxylate (D74) (0.2 mmol, 80 mg) in ethanol (10 mL) was treated with Raney Nickel, then hydrazine hydrate (2 mmol, 100 mg, 10 eq) was added dropwise over 5 min under argon at room temperature. The mixture was then heated at 45° C. for 30 min. The catalyst was then filtered off and washed with ethanol and methanol. The filtrate was concentrated under reduced pressure to give the title compound as a solid (0.16 mmol, 60 mg, 83% yield). M+H 364.3, 308.2, 264.2 (full molecule and fragments for loss of tert-butyl group and loss of Boc group).

後処理

  1. filtrationThe catalyst was then filtered off
  2. washwashed with ethanol and methanol
  3. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-f601c347bf444e4a82ceea9f2f764892
出典データセット
uspto-grants-2012_10
特許番号
US08288412B2

反応ノート

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