Acetic Acid → Tert-butyl 4-((6-bromopyridin-3-yl)amino)piperidine-1-carboxylate

HRID 1467963ノート

反応式

HRID 1467963 の反応式
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[Br:15][C:16]1[N:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(OCC)(=O)C>[Br:15][C:16]1[N:21]=[CH:20][C:19]([NH:22][CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)=[CH:18][CH:17]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 6428116-Bromopyridin-3-amineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 86602140Tert-butyl 4-((6-bromopyridin-3-yl)amino)piperidine-1-carboxylate収率 62%

試薬・触媒・溶媒 2

HCID 63651,1-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of tert-butyl 4-oxopiperidine-1-carboxylate (1.15 g, 5.78 mmol) and 6-bromopyridin-3-amine (0.5 g, 2.89 mmol) in dichloroethane (20 mL), acetic acid (8 mL, 2.89 mmol) was added and the contents were stirred at room temperature for 3 h. Sodium triacetoxy borohydride (1.225 g, 5.78 mmol) was added and the contents were stirred at room temperature for 12 h. The reaction was diluted with ethyl acetate and washed with brine; the organic layer was separated and concentrated in vacuo. The resulting residue was purified by flash column chromatography to give tert-butyl 4-((6-bromopyridin-3-yl)amino)piperidine-1-carboxylate (0.638 g, 62%); MS: 357.1 (M+1)

後処理

  1. additionwas added
  2. stirringthe contents were stirred at room temperature for 12 h
  3. washwashed with brine
  4. customthe organic layer was separated
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-095a9df2de08454da67543e86e1307a9
出典データセット
uspto-grants-2015_04
特許番号
US09000175B2

反応ノート

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