Ethanol → 1-{4-[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-fluoro-phenyl}-cyclobutanecarbonitrile

HRID 1453141노트

반응식

HRID 1453141 반응식
[CH:1]1([C:6]([OH:32])([CH2:22][C:23]2[O:24]C(C)(C)O[C:27](=[O:29])[CH:28]=2)[C:7]#[C:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:19]#[N:20])[CH2:18][CH2:17][CH2:16]3)=[C:11]([F:21])[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)C.[H][H].[OH-].[Na+]>O.[OH-].[OH-].[Pd+2].C(O)(=O)C>[CH:1]1([C:6]2([CH2:7][CH2:8][C:9]3[CH:14]=[CH:13][C:12]([C:15]4([C:19]#[N:20])[CH2:18][CH2:17][CH2:16]4)=[C:11]([F:21])[CH:10]=3)[CH2:22][C:23](=[O:24])[CH2:28][C:27](=[O:29])[O:32]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

8

반응물 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 587622991-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclobutanecarbonitrileHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 587626051-{4-[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-fluoro-phenyl}-cyclobutanecarbonitrile수율 83%

시약·촉매·용매 3

HCID 9942167Palladium hydroxide촉매HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

To a solution of 1-{4-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclobutanecarbonitrile (6.0 g, 13.7 mmol) from step 3 below was added Pd(OH)2/C (2.0 g) and ethanol (100 mL). The reaction was placed under a nitrogen atmosphere using a balloon filled with hydrogen. The slurry was stirred vigorously for 18 hours. The reaction was filtered to remove all of the solids, and the liquid was concentrated to an oil. The oil was dissolved in methanol (100 mL), and solution of NaOH (1.64 g, 41 mmol) dissolved in water (30 mL). The reaction was stirred for 18 hours, and then acetic acid (1 mL) was added. The liquid was concentrated to an oil, then redissolved in CH2Cl2, and washed with 1 N HCl. The organic layer was dried over MgSO4, filtered, and then concentrated to give the desired product (4.338 g, 83%). MS (ESI): 382 (M−H+).

후처리

  1. filtrationThe reaction was filtered
  2. customto remove all of the solids
  3. concentrationthe liquid was concentrated to an oil
  4. dissolutionThe oil was dissolved in methanol (100 mL)
  5. stirringThe reaction was stirred for 18 hours
  6. concentrationThe liquid was concentrated to an oil
  7. dissolutionredissolved in CH2Cl2
  8. washwashed with 1 N HCl
  9. dry with materialThe organic layer was dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4a9dc2cbc7054302b5164fd56ae72502
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473790B2

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