Tert-butyl (1-(2-methylbutanoyl)piperidin-4-yl)carbamate → 1-(4-Amino-1-piperidinyl)-2-methyl-1-butanone

HRID 574686ノート

反応式

HRID 574686 の反応式
[CH3:1][CH:2]([CH2:19][CH3:20])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([NH:11]C(=O)OC(C)(C)C)[CH2:7][CH2:6]1)=[O:4]>Cl.CO>[NH2:11][CH:8]1[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH:2]([CH3:1])[CH2:19][CH3:20])[CH2:6][CH2:7]1

参加物

3

反応物 1

HCID 89737189Tert-butyl (1-(2-methylbutanoyl)piperidin-4-yl)carbamate

生成物 1

HCID 167829341-(4-Amino-1-piperidinyl)-2-methyl-1-butanone収率 86.4%

試薬・触媒・溶媒 1

HCID 21893726Hydrochloride methanol溶媒

反応条件

温度
50 °C

実験手順

Protected piperidine 15 (1.2 g, 4.55 mmol) was dissolved in HCl/MeOH (2 M). The reaction mixture was stirred at 50° C. for 2 h. The crude was concentrated under vacuo and was washed with dichloromethane twice. The crude was basified by NaOH solution (6N) to pH 12. The crude was extracted by EtOAc for 6 times. The combined organic layers was evaporated under vacuo yielding final product 16 (724 mg, 3.93 mmol, 86%). H-NMR (DMSO-d6) ∂ 0.78 (q, J=6 Hz, 3H), 0.95 (t, J=5 Hz, 3H), 1.09 (m, 2H), 1.26 (m, 1H), 1.53 (m, 1H), 1.74 (m, 2H), 2.67 (m, 2H), 2.80 (br, 1H), 3.03 (br, 1H), 3.87 (d, J=12 Hz, 1H), 4.23 (br, 1H).

後処理

  1. concentrationThe crude was concentrated under vacuo
  2. washwas washed with dichloromethane twice
  3. extractionThe crude was extracted by EtOAc for 6 times
  4. customThe combined organic layers was evaporated under vacuo

出典と根拠

ORDレコード
ord-403e7a6452264e0abb9af5728cf4f6d6
出典データセット
uspto-grants-2015_05
特許番号
US09034903B2

反応ノート

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