Diethyl Ether → tert-Butyl 4-formylpiperidine-1-carboxylate

HRID 29755

反応式

HRID 29755 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OCC)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 3283Diethyl EtherHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

生成物 1

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylate収率 81.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Periodinane (26.9 g, 63.5 mmol) was added to 4-Hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (10.5 g, 48.8 mmol) in CH2Cl2 (200 mL) and stirred for 90 min. Diethyl ether (560 mL) was added and precipitates were removed by extraction with 10% Na2S2O3/saturated NaHCO3 (1:1, 300 mL). The organic layer was washed with 0.5 M NaOH solution and brine. The organic phase was dried and concentrated under reduced pressure. Purification using flash chromatography (hexane/EtOAc, 8:2) gave 4-Formyl-piperidine-1-carboxylic acid tert-butyl ester (8.5 g, 81%).

後処理

  1. customprecipitates
  2. customwere removed by extraction with 10% Na2S2O3/saturated NaHCO3 (1:1, 300 mL)
  3. washThe organic layer was washed with 0.5 M NaOH solution and brine
  4. customThe organic phase was dried
  5. concentrationconcentrated under reduced pressure
  6. customPurification

出典と根拠

ORDレコード
ord-6d1f1c34797f4942b98da336563f4545
出典データセット
uspto-grants-2008_09
特許番号
US07423012B2

関連ノート

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