Methanesulfonic acid 1-(3-benzyloxy-1-methyl-4-oxo-1,4-dihydro-pyridin-2-yl)-2,2,2-trifluoro-ethyl ester → 3-Hydroxy-1-methyl-2-(2,2,2-trifluoroethyl)-4(1H)-pyridinone

HRID 1187480ノート

反応式

HRID 1187480 の反応式
C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH3:16])[C:10]=1[CH:17](OS(C)(=O)=O)[C:18]([F:21])([F:20])[F:19])C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[OH:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH3:16])[C:10]=1[CH2:17][C:18]([F:21])([F:19])[F:20]

参加物

5

反応物 2

HCID 86623501Methanesulfonic acid 1-(3-benzyloxy-1-methyl-4-oxo-1,4-dihydro-pyridin-2-yl)-2,2,2-trifluoro-ethyl esterHCID 178418361HCID 178418361、化合物

生成物 1

HCID 249445483-Hydroxy-1-methyl-2-(2,2,2-trifluoroethyl)-4(1H)-pyridinone収率 9.7%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A mixture of methanesulfonic acid 1-(3-benzyloxy-1-methyl-4-oxo-1,4-dihydro-pyridin-2-yl)-2,2,2-trifluoro-ethyl ester (2.80 g, 7.15 mmol) and 10% Pd/C (0.56 g) in ethyl alcohol was subjected to hydrogenation in a Parr apparatus under 50 psi hydrogen pressure for 90 min. The mixture was filtered through a pad of CELITE™, and the filtrate was concentrated to dryness. The residue was purified by flash column chromatography on silica gel using a mixture of isopropyl alcohol and a conc. NH4OH solution (90/10, v/v) as eluant. Fractions rich in the product were pooled together and evaporated to dryness, thereby affording 3-hydroxy-1-methyl-2-(2,2,2-trifluoro-ethyl)-1H-pyridin-4-one (first crop: 143 mg, 9.7% yield, second crop: 240 mg, 16.2% yield). 1H NMR (90 MHz, CD3OD) δ (ppm): 7.66 (d, J=7.2 Hz, 1H), 6.41 (d, J=7.4 Hz, 1H), 3.89 (q, J=10.2 Hz, 1H) and 3.82 (s, 3H); MS-ESI (m/z): 208 [M+1]+, 188.2, 168.2. HPLC purity (peak area percent) of both fractions are about 98% at λ=254 nm, RT=3.75 min (HPLC method is described in Part A above).

後処理

  1. filtrationThe mixture was filtered through a pad of CELITE™
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was purified by flash column chromatography on silica gel using
  4. additiona mixture of isopropyl alcohol
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-56b9a3f7009548fd81a0d03f23b7c651
出典データセット
uspto-grants-2014_03
特許番号
US08673943B2

反応ノート

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