Diethyl Ether → (1-Formylcyclopropyl)carbamic acid tert-butyl ester

HRID 256256

反応式

HRID 256256 の反応式
[C:1]([NH:8][C:9]1([C:12](O)=[O:13])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].CN1CCNCC1[Al+]C1CNCCN1C.CCOCC>O1CCCC1>[C:1]([NH:8][C:9]1([CH:12]=[O:13])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 18792082Bis(1-methylpiperazin-2-yl)alumanylium;hydride

生成物 1

HCID 10352385(1-Formylcyclopropyl)carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

N-Boc-1-amino-1-cyclopropanecarboxylic acid is dissolved in tetrahydrofuran and stirred at 0° C. under argon. Bis(N-methylpiperazinyl)aluminum hydride is added and the reaction mixture is heated to reflux overnight. Ether is then added, and the excess hydride is quenched with saturated NaCl. The aqueous phase is separated and extracted with ether. The combined organic phases are washed with 2M NaOH, 2M HCl and saturated NaCl. The solution is dried over Na2SO4 and evaporated to yield N-Boc-1-amino-1-cyclopropanecarboxaldehyde.

後処理

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux overnight
  3. customthe excess hydride is quenched with saturated NaCl
  4. customThe aqueous phase is separated
  5. extractionextracted with ether
  6. washThe combined organic phases are washed with 2M NaOH, 2M HCl and saturated NaCl
  7. dry with materialThe solution is dried over Na2SO4
  8. customevaporated

出典と根拠

ORDレコード
ord-09ba152299a341178c810e4e2124543b
出典データセット
uspto-grants-1987_10
特許番号
US04701552

関連ノート

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