Water → tert-butyl 2-chloro-4-methyl-5-oxo-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

HRID 80825

反応式

HRID 80825 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[CH2:8][N:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:6][CH2:5][C:4]=2[N:3]=1.[OH2:20]>CCOC(C)=O.[Cl-].[Na+].O.[Ru](Cl)(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:8](=[O:20])[N:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:6][CH2:5][C:4]=2[N:3]=1

参加物

6

反応物 2

HCID 962WaterHCID 86690273tert-butyl 2-chloro-4-methyl-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

生成物 1

HCID 86690274tert-butyl 2-chloro-4-methyl-5-oxo-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

試薬・触媒・溶媒 3

HCID 61850Ruthenium trichloride触媒HCID 8857Ethyl Acetate溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

To a suspension of ruthenium trichloride (0.141 g, 0.681 mmol) and NaI04 (8.32 g, 38.9 mmol) in H2O (30 mL) at 0° C., a solution of tert-butyl 2-chloro-4-methyl-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (2.75 g, 9.73 mmol) in EtOAc (30 mL) was added. After stirring for 5 min., the reaction mixture was warmed up to rt and stirred. After stirring for 21.5 h, the mixture was diluted with EtOAc and brine. The organic layer was separated, dried over Na2SO4, filtered, and concentrated. The crude was purified by flash column chromatography on 80 g of silica gel (with 25 g pre-column of silica gel; eluent: heptane/EtOAc=100:0 to 70:30) to give tert-butyl 2-chloro-4-methyl-5-oxo-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (2.10 g) as a white solid: 1H NMR (400 MHz, CDCl3) δ ppm 7.15 (s, 1H), 3.98 (t, J=6.32 Hz, 2 H), 3.13 (t, J=6.32 Hz, 2 H), 2.70 (s, 3 H), 1.58 (s, 9 H).

後処理

  1. stirringstirred
  2. stirringAfter stirring for 21.5 h
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified by flash column chromatography on 80 g of silica gel (with 25 g pre-column of silica gel; eluent: heptane/EtOAc=100:0 to 70:30)

出典と根拠

ORDレコード
ord-3d827cf773ca4ee4bb76c9575b7d598c
出典データセット
uspto-grants-2014_09
特許番号
US08846656B2

関連ノート

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