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

HRID 730748ノート

反応式

HRID 730748 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178420582HCID 178420582、化合物触媒HCID 1140Toluene溶媒

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-0fc097a1b1004ed6816af4ba0c676935
出典データセット
uspto-grants-2009_09
特許番号
US07582761B2

反応ノート

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