Ethyl 4-piperidinecarboxylate → 4'-[2-(2-Chloro-4-trifluoromethanesulfonyloxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carboxylic acid ethyl ester

HRID 1097928ノート

反応式

HRID 1097928 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([O:23][S:24]([C:27]([F:30])([F:29])[F:28])(=[O:26])=[O:25])[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:22])[C:9]([C:15]1[CH:20]=[CH:19][N:18]=[C:17](Cl)[CH:16]=1)([OH:14])[C:10]([F:13])([F:12])[F:11].[CH2:31]([O:33][C:34]([CH:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)=[O:35])[CH3:32]>CN1CCCC1=O.O>[CH2:31]([O:33][C:34]([CH:36]1[CH2:41][CH2:40][N:39]([C:17]2[CH:16]=[C:15]([C:9]([OH:14])([C:10]([F:12])([F:11])[F:13])[CH:8]([C:7]3[CH:6]=[CH:5][C:4]([O:23][S:24]([C:27]([F:28])([F:29])[F:30])(=[O:25])=[O:26])=[CH:3][C:2]=3[Cl:1])[CH3:22])[CH:20]=[CH:19][N:18]=2)[CH2:38][CH2:37]1)=[O:35])[CH3:32]

参加物

5

反応物 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 86629107Trifluoro-methanesulfonic acid 3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenyl ester

生成物 1

HCID 866291084'-[2-(2-Chloro-4-trifluoromethanesulfonyloxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carboxylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

Trifluoro-methanesulfonic acid 3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenyl ester (Example 135-Step 1, 1.0 g) and piperidine-4-carboxylic acid ethyl ester (0.773 mL) in 1-methyl-2-pyrrolidon (10 mL) were heated at 220° C. in a microwave oven for 30 minutes. The reaction mixture was then diluted with water (100 mL), extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (70 g silica gel, heptane/acetic acid isopropylester 80/20 to 70/30) to give the title compound as light yellow viscous oil (119 mg). MS (m/e)=619.2 (MH+).

後処理

  1. customwere heated at 220° C. in a microwave oven for 30 minutes
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (70 g silica gel, heptane/acetic acid isopropylester 80/20 to 70/30)

出典と根拠

ORDレコード
ord-255f816562594ac3ba58020d5597343b
出典データセット
uspto-grants-2012_03
特許番号
US08143280B2

反応ノート

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