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

HRID 1095066ノート

反応式

HRID 1095066 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]([CH2:30]Br)[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]([CH2:30][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 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate

生成物 1

HCID 577431634-(2-Formyl-4-iodo-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl ester収率 63%

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 (2 g, 8.2 mmol) (Aldrich) in N,N-dimethylformamide (20 mL) was added anhydrous K2CO3 (1.15 g, 8.2 mmol), and 4-bromomethyl-piperidine -1-carboxylic acid tert-butyl ester (2.3 g, 8.2 mmol, Pharmacore). The reaction mixture was heated at 60° C. for 18 h. The crude was cooled to room temperature, diluted with ethyl acetate, washed with water, brine. The organic layer was separated, dried over MgSO4, concentrated to give 4-(2-formyl-4-iodo-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl ester (Yield 2.3 g, 63%).

後処理

  1. temperatureThe crude was cooled to room temperature
  2. washwashed with water, brine
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-af5f65185357411ead3f1547b498ad26
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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