Potassium Carbonate → (R)-3-(2-Nitrophenylamino)piperidine-1-carboxylic acid tertbutyl ester

HRID 242818

반응식

HRID 242818 반응식
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH2:21][C@@H:20]([NH2:24])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH2:21][C@@H:20]([NH:24][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylate

생성물 1

HCID 59073577(R)-3-(2-Nitrophenylamino)piperidine-1-carboxylic acid tertbutyl ester수율 77.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

A mixture of 1-fluoro-2-nitrobenzene (1.41 g, 10.0 mmol), (R)-3-aminopiperidine-1-carboxylic acid tertbutyl ester (2 g, 10.0 mmol) and potassium carbonate (152 mg, 11.0 mmol) in DMF (18 mL) was heated to 120° C. under microwave irradiation for 30 min. The reaction mixture was partitioned between EtOAc (150 mL) and water. The organic layer was washed with brine, dried (Na2SO4) and then concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, eluant 10% EtOAc in DCM) affording (R)-3-(2-Nitrophenylamino)piperidine-1-carboxylic acid tertbutyl ester as an orange oil (2.48 g, 77%). LCMS: RT 3.95 min [M+H-tBu]+ 266.2.

후처리

  1. customThe reaction mixture was partitioned between EtOAc (150 mL) and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography (Si—PCC, eluant 10% EtOAc in DCM)

출처 및 근거

ORD 기록
ord-f0deb9b4db2e463f80f81f0487975eb6
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653089B2

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