p-Fluoronitrobenzene → tert-butyl [(3R)-1-(4-nitrophenyl)pyrrolidin-3-yl]carbamate

HRID 1441364ノート

反応式

HRID 1441364 の反応式
[NH:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:9]([O:8][C:7](=[O:13])[NH:6][C@@H:3]1[CH2:4][CH2:5][N:1]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH2:2]1)([CH3:10])([CH3:12])[CH3:11]

参加物

5

反応物 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine

生成物 1

HCID 86594863tert-butyl [(3R)-1-(4-nitrophenyl)pyrrolidin-3-yl]carbamate収率 97.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

tert-Butyl(3R)-pyrrolidin-3-ylcarbamate (4.54 g, 24.4 mmol), 4-fluoronitrobenzene (3.78 g, 24 mmol) and potassium carbonate (3.54 g 25.6 mmol) in acetonitrile (70 ml) were heated under reflux for 18 hours. After evaporation under reduced pressure, the mixture was dissolved in DCM (200 ml), and washed with water (100 ml) and saturated sodium chloride solution (25 ml). The solution was dried and filtered. After evaporation under reduced pressure, chromatography on silica gel eluting with DCM gave the title compound (7.19 g, 97%). NMR: 1.39 (s, 9H), 1.87-1.98 (m, 1H), 2.09-2.21 (m, 1H), 3.15-3.23 (m, 1H), 3.32-3.44 (m, 1H), 3.45-3.51 (m, 1H), 3.53-3.61 (m, 1H), 4.09-4.21 (m, 1H), 6.57 (d, 2H), 7.21 (s, 1H), 8.01 (d, 2H); m/z (MH+—C4H8) 252.

後処理

  1. temperatureunder reflux for 18 hours
  2. customAfter evaporation under reduced pressure
  3. dissolutionthe mixture was dissolved in DCM (200 ml)
  4. washwashed with water (100 ml) and saturated sodium chloride solution (25 ml)
  5. customThe solution was dried
  6. filtrationfiltered
  7. customAfter evaporation under reduced pressure, chromatography on silica gel eluting with DCM

出典と根拠

ORDレコード
ord-eda7af133160438ba551684c975ce4c0
出典データセット
uspto-grants-2010_02
特許番号
US07655652B2

反応ノート

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