Triethylamine → tert-Butyl 4-(5-nitropyridine-2-ylamino)piperidine-1-carboxylate

HRID 1691867ノート

反応式

HRID 1691867 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([NH2:24])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>CN(C)C=O>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([NH:24][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 782402-Bromo-5-nitropyridineHCID 12682914-Amino-1-Boc-piperidine

生成物 1

HCID 53255493tert-Butyl 4-(5-nitropyridine-2-ylamino)piperidine-1-carboxylate収率 90.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 2-bromo-5-nitro-pyridine (5 g, 24.6 mmol), 4-amino-piperidine-1-carboxylic acid tert-butyl ester (5 g, 25 mmol), and triethylamine (5 mL) in N,N-dimethylformamide (30 mL) was stirred at 90° C. for 14 h. The reaction mixture was then partitioned between water and ethyl acetate, and the two layers were separated. The aqueous layer was extracted with ethyl acetate three times. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography to give 7.15 g (90%) 4-(5-nitro-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester as a yellow solid. LCMS calcd for C15H22N4O4 (m/e) 322, obsd 323 (M+H).

後処理

  1. customThe reaction mixture was then partitioned between water and ethyl acetate
  2. customthe two layers were separated
  3. extractionThe aqueous layer was extracted with ethyl acetate three times
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-00aa8268c1eb4ce8a89909767c19be69
出典データセット
uspto-grants-2012_04
特許番号
US08153644B2

反応ノート

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