HCID 67281584、化合物 → HCID 67282784、化合物

HRID 913021ノート

反応式

HRID 913021 の反応式
C([O:8][C:9]1[C:10](=[O:22])[CH:11]=[C:12]([CH:16]([OH:21])[C:17]([F:20])([F:19])[F:18])[N:13]([CH3:15])[CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[C:10](=[O:22])[CH:11]=[C:12]([CH:16]([OH:21])[C:17]([F:18])([F:19])[F:20])[N:13]([CH3:15])[CH:14]=1

参加物

4

反応物 1

HCID 67281584HCID 67281584、化合物

生成物 1

HCID 67282784HCID 67282784、化合物収率 92%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒2 回

実験手順

A mixture of 5-benzyloxy-1-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (3.1 g, 9.9 mmol) and methanol (60 mL) was sonicated to give a clear solution. To the solution was added Pd/C (10 wt. %, dry basis, on activated carbon, wet, Degussa type E101 NE/W, 0.58 g). The debenzylation reaction was conducted in a Parr hydrogenator under an atmosphere of hydrogen pressurized to 50 psi. The reaction was completed within 20 min. The reaction mixture was diluted with MeOH (100 mL), sonicated for about 20 min. A CELITE™ bed was prepared on a sintered glass, and washed with 6M HCl (100 mL), followed by water (7×50 mL) and then methanol (2×50 mL) under suction. The reaction mixture was filtered through the pre-treated CELITE™ bed. The filtrate was collected and concentrated in vacuo to give 5-hydroxy-1-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one as a solid product (2.05 g, 92% yield, HPLC Method 1 (Example 24), RT=7.4 min, HPLC purity (peak percent area): 99.4% at λ=280 nm). 1H NMR (DMSO-d6+D2O) δ ppm: 7.50 (s, 1H), 6.50 (s, 1H), 5.37 (q, J=6.5 Hz, 1H), 3.67 (s, 3H); MS-ESI (m/z) 224.2 [M+1]+, 206.2, 155.2 (100%), 140.1, 126.1.

後処理

  1. customwas sonicated
  2. customto give a clear solution
  3. customThe debenzylation reaction
  4. customsonicated for about 20 min
  5. customA CELITE™ bed was prepared on a sintered glass
  6. washwashed with 6M HCl (100 mL)
  7. filtrationThe reaction mixture was filtered through the pre-treated CELITE™ bed
  8. customThe filtrate was collected
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4210e50cb5b44d2ebecd10f807870e77
出典データセット
uspto-grants-2011_09
特許番号
US08026261B2

反応ノート

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