tert-Butyl 4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-3-oxopiperazine-1-carboxylate → 1-[2-(1,3-Dihydro-4-methyl-1-oxo-5-isobenzofuranyl)ethyl]-2-piperazinone

HRID 1466064ノート

反応式

HRID 1466064 の反応式
O[CH:2]([C:18]1[CH:27]=[CH:26][C:21]2[C:22](=[O:25])[O:23][CH2:24][C:20]=2[C:19]=1[CH3:28])[CH2:3][N:4]1[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][C:5]1=[O:17]>CO.[OH-].[OH-].[Pd+2]>[CH3:28][C:19]1[C:20]2[CH2:24][O:23][C:22](=[O:25])[C:21]=2[CH:26]=[CH:27][C:18]=1[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][C:5]1=[O:17]

参加物

4

反応物 1

HCID 89526106tert-Butyl 4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-3-oxopiperazine-1-carboxylate

生成物 1

HCID 895334771-[2-(1,3-Dihydro-4-methyl-1-oxo-5-isobenzofuranyl)ethyl]-2-piperazinone

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 887Methanol溶媒

実験手順

A solution of tert-butyl 4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-3-oxopiperazine-1-carboxylate (160 mg, 0.41 mmol) in 20 mL of MeOH was treated with Pd(OH)2 (120 mg, 0.21 mmol) was stirred under 40 psi atmosphere of H2 at 60 C. After 18 hrs the solution was filtered through a pad of celite which was subsequently washed with EtOAc. The filtrate was concentrated and the residue was then redissolved in 2 mL of DCM was treated with 4 mL of 4N HCl in dioxane at room temperature. After 2 hours excess solvent was removed and the residue partitioned between 3 mL of 1N NaOH and 10 mL of 10% IPA/Chloroform. The organic layer was collected, dried over magnesium sulfate, filtered and concentrated to give the title product. The free amine was used without further purification. 1H NMR (500 MHz; CDCl3): 7.82 (m, 2H), 5.40 (dd, J=2.3, 8.0 Hz, 1H), 5.27 (s, 1H), 3.74-3.70 (m, 1H), 3.61 (s, 2H), 3.45-3.41 (m, 1H), 3.38-3.34 (m, 1H), 3.26-3.22 (m, 1H), 3.04-3.01 (m, 2H), 2.06 (s, 3H).

後処理

  1. filtrationAfter 18 hrs the solution was filtered through a pad of celite which
  2. washwas subsequently washed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe residue was then redissolved in 2 mL of DCM
  5. additionwas treated with 4 mL of 4N HCl in dioxane at room temperature
  6. customAfter 2 hours excess solvent was removed
  7. customthe residue partitioned between 3 mL of 1N NaOH and 10 mL of 10% IPA/Chloroform
  8. customThe organic layer was collected
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-7262a0518460444987052e0e2d993803
出典データセット
uspto-grants-2015_04
特許番号
US08999990B2

反応ノート

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