Ethyl Acetate → 5-Amino-4-fluoro-2-(1-methylcyclohexyl)phenyl methyl carbonate

HRID 471986ノート

反応式

HRID 471986 の反応式
[C:1](=[O:22])([O:20][CH3:21])[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([F:12])=[CH:5][C:4]=1[C:13]1([CH3:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C([O-])=O.[NH4+].C(OCC)(=O)C>CO.[Pd]>[C:1](=[O:22])([O:20][CH3:21])[O:2][C:3]1[CH:8]=[C:7]([NH2:9])[C:6]([F:12])=[CH:5][C:4]=1[C:13]1([CH3:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 2723923Ammonium formateHCID 593950134-Fluoro-2-(1-methylcyclohexyl)-5-nitrophenyl methyl carbonate

生成物 1

HCID 513584455-Amino-4-fluoro-2-(1-methylcyclohexyl)phenyl methyl carbonate収率 82.1%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

To a solution of 4-fluoro-2-(1-methylcyclohexyl)-5-nitrophenyl methyl carbonate 24.1 g, 77.5 mmol) in 220 mL of CH3OH was added Pd/C 10%, 9.6 g, then ammonium formate (26.7 g, 445 mmol) was portion-wise added to the above reaction mixture at room temperature until starting material is consumed. The mixture was filtrated and the filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel diluted with hexane:ethyl acetate=50:1 to give 5-amino-4-fluoro-2-(1-methylcyclohexyl)phenyl methyl carbonate as a red brown oil (17.9 g, 82% yield). 1H NMR (400 MHz, CDCl3) δ 6.99 (d, J=13.6 Hz, 1H), 6.51 (d, J=8.4 Hz, 1H), 3.89 (s, 3H), 3.43 (brs, 2H), 1.96-1.91 (m, 2H), 1.58-1.38 (m, 8H), 1.18 (s, 3H): MS m/z: 281.9 [M+H]

後処理

  1. additionadded to the above reaction mixture at room temperature
  2. customis consumed
  3. filtrationThe mixture was filtrated
  4. customthe filtrate was evaporated under vacuum
  5. customThe residue was purified by column chromatography on silica gel
  6. additiondiluted with hexane

出典と根拠

ORDレコード
ord-4ee6b286ce0046298c47b6fae48d6e40
出典データセット
uspto-grants-2014_01
特許番号
US08633189B2

反応ノート

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