Cyclopentanone → 2-(2-Fluoro-pyridin-4-yl)-2-cyclo-pentylamino-1-(3-trifluoromethyl-phenyl)-ethanol

HRID 1884814ノート

反応式

HRID 1884814 の反応式
[NH2:1][CH:2]([C:15]1[CH:20]=[CH:19][N:18]=[C:17]([F:21])[CH:16]=1)[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)[OH:4].[C:22]1(=O)[CH2:26][CH2:25][CH2:24][CH2:23]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[F:21][C:17]1[CH:16]=[C:15]([CH:2]([NH:1][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:12])([F:13])[F:14])[CH:6]=2)[OH:4])[CH:20]=[CH:19][N:18]=1

参加物

6

反応物 4

HCID 8452CyclopentanoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 155242512-Amino-2-(2-fluoropyridine-4-yl)-1-(3-trifluoromethylphenyl)ethanol

生成物 1

HCID 155242522-(2-Fluoro-pyridin-4-yl)-2-cyclo-pentylamino-1-(3-trifluoromethyl-phenyl)-ethanol収率 92%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

The 2 -amino-2-(2-fluoro-pyridin-4-yl)- 1 -(3-trifluoromethyl-phenyl)-ethanol (5) (1.0 g, 3.3 mmol), cyclopentanone (0.42 g, 5.0 mmol), and Na(OAc)3BH (1.4 g, 6.7 mmol) in 1,2 dichloroethane (20 mL) were stirred under argon at RT for 15 hrs. The resulting mixture was treated with sat. aqueous NaHCO3 (50 mL), extracted with ethyl acetate (3×75 mL), dried (sodium sulfate), and concentrated. The resulting residue was purified by silica gel chromatography using 50% ethyl acetate in methylene chloride to give the title product (1.1 g, 92%). 1H NMR (300 MHz, CDCl3) d 8.05 (d, J=4.9 Hz, 1 H, Pyr), 7.51 (d, J=7.9 Hz, 1 H, Ar), 7.36 (t, J=7.8 Hz, 1 H, Ar), 7.32 (s, 1 H, Ar), 7.22 (d, J=7.9 Hz, 1 H, Ar), 6.81 (d, J=4.9 Hz, 1 H, Pyr), 6.64 (s, 1 H, Pyr), 5.00 (d, J=4.6 Hz, 1 H, PhCHOH), 4.01 (d, J=4.9 Hz, 1 H, CHCHNH), 2.99 (quin, J=3.0 Hz, 1 H, CH2CHCH2), 1.85-1.25 (m, 8 H, CH2).

後処理

  1. extractionextracted with ethyl acetate (3×75 mL)
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-a17c0a4a29f64444ac14e60f4ba89667
出典データセット
uspto-grants-2004_07
特許番号
US06767908B2

反応ノート

読み込み中…