Sodium Chloride → (1-Formylcyclopropyl)carbamic acid tert-butyl ester

HRID 2118472Notes

Reaction equation

HRID 2118472 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.[H-].[Na+].[Cl-]>O1CCCC1.CCOCC>[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

7

Reactant 4

HCID 5234Sodium ChlorideHCID 166653HydrideHCID 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 2

HCID 3283Diethyl EtherSolventHCID 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 quenced 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 aqueous phase is separated
  4. extractionextracted with ether
  5. washThe combined organic phases are washed with 2M NaOH, 2M HCl and saturated NaCl
  6. dry with materialThe solution is dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-63e34411b3ea4a11b39e763a8fadaea1
Source dataset
uspto-grants-1987_07
Patent number
US04678675

Reaction notes

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