Red-Al → 4-(3,5-Difluoro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 912807노트

반응식

HRID 912807 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([F:20])=[CH:18][C:17]([F:21])=[C:16](F)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COCCO[AlH2-]OCCOC.[Na+]>C1(C)C=CC=CC=1.[Cl-].[Cl-].C1([Ti+2]C2C=CC=C2)C=CC=C1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:19]([F:20])=[CH:18][C:17]([F:21])=[CH:16][N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 16684438Red-AlHCID 67398573Tert-butyl 4-(3,5,6-trifluoropyridin-2-yl)piperazine-1-carboxylate

생성물 1

HCID 674014754-(3,5-Difluoro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 178420582HCID 178420582, 화합물촉매HCID 1140Toluene용매

실험 절차

(Analogous to the procedure of Hee-Gweon Woo; Bo-Hye, Kim and Sun-Jung Song, Bull. Korean Chem. Soc. 1999, 20, 865-866). 4-(3,5,6-Trifluoro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester from step (a) above (950 mg, 3 mmol) was added to a mixture of bis(cyclopentadienyl)titanium dichloride (37 mg, 0.15 mmol, Aldrich) and Red-Al (1.32 mL, Aldrich) in toluene (3 mL). The reaction mixture was stirred at room temperature for 3 h and quenched by the addition of water (50 mL). The mixture was extracted with EtOAc (2×40 mL) and the combined organic phases were washed with brine (50 mL), dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 20% EtOAc/hexane to give the title compound as a light-yellow oil. MS (ESI, pos. ion) m/z: 300 (M+1).

후처리

  1. customquenched by the addition of water (50 mL)
  2. extractionThe mixture was extracted with EtOAc (2×40 mL)
  3. washthe combined organic phases were washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by silica gel chromatography
  8. washeluting with 20% EtOAc/hexane

출처 및 근거

ORD 기록
ord-d411c2838ff14a84aff82541adc2efab
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026241B2

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