Potassium Carbonate → 4-(2-Formyl-4-iodo-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1095067ノート

反応式

HRID 1095067 の反応式
[I:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>CN(C)C=O.C(OCC)(=O)C>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([O:10][C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:9][C:6]=2[CH:7]=[O:8])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 2526125-IodosalicylaldehydeHCID 157347131-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine

生成物 1

HCID 577432744-(2-Formyl-4-iodo-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester収率 84%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a solution of 5-iodosalicylaldehyde (3 g, 12.1 mmol) (Aldrich) in N,N-dimethylformamide (20 mL) was added anhydrous K2CO3 (5 g, 36.3 mmol), and 4-(toluene-4-sulfonyloxy)-piperidine-1-carboxylic acid tert-butyl ester (5.4 g, 18.1 mmol, ASTATECH). The reaction mixture was heated at 60° C. for 18 h. The mixture was cooled to room temperature, diluted with ethyl acetate, washed with water. The organic layer was separated, the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with water, brine, dried over MgSO4, and concentrated to give crude 4-(2-formyl-4-iodo-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester as a yellow oil (Yield 4.38 g, 84%).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-cc2c979b317247feb5c24eb3d60a086a
出典データセット
uspto-grants-2012_03
特許番号
US08134001B2

反応ノート

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