Dimethylformamide → Methyl 4-[(4-hydroxypiperidin-1-yl)methyl]-3-isopropoxybenzoate

HRID 507988ノート

反応式

HRID 507988 の反応式
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH:14]([CH3:16])[CH3:15].[OH:17][CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[OH:17][CH:18]1[CH2:23][CH2:22][N:21]([CH2:2][C:3]2[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=2[O:13][CH:14]([CH3:16])[CH3:15])[CH2:20][CH2:19]1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 23157338HCID 23157338、化合物

生成物 1

HCID 23157343Methyl 4-[(4-hydroxypiperidin-1-yl)methyl]-3-isopropoxybenzoate収率 83%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

A mixture of methyl 4-(bromomethyl)-3-isopropoxybenzoate (2.0 g, 6.96 mmol), 4-hydroxypiperidine (1.06 g, 10.4 mmol), potassium carbonate (1.44 g, 10.4 mmol) and N,N-dimethylformamide (20 mL) was stirred at 70° C. for 20 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, hexane/ethyl acetate=10/1-hexane/ethyl acetate=1/2) to give the title compound (1.77 g, yield 83%) as a pale-yellow oil.

後処理

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (basic silica gel, hexane/ethyl acetate=10/1-hexane/ethyl acetate=1/2)

出典と根拠

ORDレコード
ord-c3b48a72b5684cd680c808926deac83c
出典データセット
uspto-grants-2010_08
特許番号
US07786165B2

反応ノート

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