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

HRID 1441364노트

반응식

HRID 1441364 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-eda7af133160438ba551684c975ce4c0
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07655652B2

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