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

HRID 1467963

반응식

HRID 1467963 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 63651,1-Dichloroethane용매HCID 8857Ethyl Acetate용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-095a9df2de08454da67543e86e1307a9
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000175B2

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