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

HRID 1906645Notes

Reaction equation

HRID 1906645 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4d42849dd06c46e28426471b3a77a30a
Source dataset
uspto-grants-1987_03
Patent number
US04652676

Reaction notes

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