2,4-Difluoronitrobenzene → (S)-tert-butyl 3-(5-fluoro-2-nitrophenoxy)piperidine-1-carboxylate

HRID 240593노트

반응식

HRID 240593 반응식
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:11]([N:18]1[CH2:23][CH2:22][CH2:21][C@H:20]([OH:24])[CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].F[C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[N+:33]([O-:35])=[O:34]>C1COCC1>[F:32][C:30]1[CH:29]=[CH:28][C:27]([N+:33]([O-:35])=[O:34])=[C:26]([CH:31]=1)[O:24][C@H:20]1[CH2:21][CH2:22][CH2:23][N:18]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:19]1

참가 물질

5

반응물 3

HCID 679672,4-DifluoronitrobenzeneHCID 1514399tert-butyl (3S)-3-hydroxypiperidine-1-carboxylateHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 58413048(S)-tert-butyl 3-(5-fluoro-2-nitrophenoxy)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

LiHMDS 1M solution in THF (6.4 ml) was added into a solution of (S)-1-Boc-3-hydroxypiperidine (1.3 g) in anhydrous THF (20.0 ml). The reaction was stirred at 0° C. for 0.5 h. Then 2,4-difluoro-1-nitro-benzene (703 μl) was added in a single portion. The reaction was allowed to warm to room temperature overnight when TLC indicated the consumption of the starting material. The reaction was quenched by addition of sat NH4Cl (5.0 ml) and diluted with EtOAc (100.0 ml). The organic layer was washed with sat. NH4Cl (50.0 ml) and the aqueous back extracted with EtOAc. The combined organic phases were washed with brine, dried, filtered and concentrated in vacuo. The residue was purified by chromatography to give the intended product.

후처리

  1. temperatureto warm to room temperature overnight when TLC
  2. customthe consumption of the starting material
  3. customThe reaction was quenched by addition of sat NH4Cl (5.0 ml)
  4. additiondiluted with EtOAc (100.0 ml)
  5. washThe organic layer was washed with sat. NH4Cl (50.0 ml)
  6. extractionthe aqueous back extracted with EtOAc
  7. washThe combined organic phases were washed with brine
  8. customdried
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by chromatography
  12. customto give the intended product

출처 및 근거

ORD 기록
ord-c87fc213343f4e9686a2ea816111b1b2
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648068B2

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