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

HRID 242818

反応式

HRID 242818 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f0deb9b4db2e463f80f81f0487975eb6
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

関連ノート

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