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3-Fluoro-5-(trifluoromethyl)benzaldehyde → 2-{5-[1-(3-Fluoro-5-trifluoromethyl-benzyl)-piperidin-4-yl]-4'-trifluoromethyl-biphenyl-3-yl}-4-methyl-pentanoic acid ethyl ester

HRID 889751
ノート
印刷プレビュー

反応式

HRID 889751 の反応式
[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:10]1[CH:11]=[C:12]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2].[F:33][C:34]1[CH:35]=[C:36]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1)[CH:37]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:10]1[CH:11]=[C:12]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:24][CH:23]=2)[CH:13]=[C:14]([CH:16]2[CH2:17][CH2:18][N:19]([CH2:37][C:36]3[CH:39]=[C:40]([C:42]([F:43])([F:44])[F:45])[CH:41]=[C:34]([F:33])[CH:35]=3)[CH2:20][CH2:21]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6056863-Fluoro-5-(trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 576660434-Methyl-2-(5-piperidin-4-yl-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

生成物 1

HCID 576660322-{5-[1-(3-Fluoro-5-trifluoromethyl-benzyl)-piperidin-4-yl]-4'-trifluoromethyl-biphenyl-3-yl}-4-methyl-pentanoic acid ethyl ester

試薬・触媒・溶媒 1

HCID 11
1,2-Dichloroethane
溶媒

実験手順

To a solution of a mixture of 4-methyl-2-{5-piperidin-4-yl-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester and methyl ester (68b) (40 mg, 0.09 mmol) in 1,2-dichloroethane (2.0 mL) was added 3-fluoro-5-trifluoromethyl-benzaldehyde (19 mg, 0.10 mmol) and sodiumtriacetoxyborohydride (25 mg, 0.12 mmol). The mixture was stirred for 14 h at room temperature. The reaction was quenched with water and extracted with dichloromethane. The organic was washed with saturated aqueous NaHCO3 solution and brine. The organic fraction was dried (MgSO4) and concentrated in vacuo. The crude mixture contained 2-{5-[1-(3-fluoro-5-trifluoromethyl-benzyl)-piperidin-4-yl]-4′-trifluoromethyl-biphenyl-3-yl}-4-methyl-pentanoic acid ethyl ester and methyl ester. Calcd for C33H34F7NO2 (M+H) 610.62, Found 610.30 (methyl ester) and Calcd for C34H36F7NO2 (M+H) 624.64, Found 624.24 (ethyl ester).

後処理

  1. customThe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. washThe organic was washed with saturated aqueous NaHCO3 solution and brine
  4. dry with materialThe organic fraction was dried (MgSO4)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ac3f6c136b1640209a7db71dd526f577
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08252935B2

反応ノート

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