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

HRID 907646Notes

Reaction equation

HRID 907646 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1([C:11](=[O:16])N(OC)C)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CCOCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1([CH:11]=[O:16])[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 15234151Tert-butyl 1-(methoxy(methyl)carbamoyl)cyclopropylcarbamateHCID 21226445Aluminium lithium hydride

Product 1

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

Procedure

To a 0.05 M solution of [1-(methoxy-methyl-carbamoyl)cyclopropyl]carbamic acid tert-butyl ester in Et2O (80 mL, 4.0 mmol) at room temperature was added dropwise lithium aluminum hydride (1.0 M in Et2O, 5 mL, 5.0 mmol). The reaction mixture was stirred for another 20 min and then quenched with 6 mL of a solution of KHSO4 in water. The layers were separated and the aqueous layer was extracted with Et2O. The combined organic layers were washed with 1 N HCl, saturated NaHCO3, and brine, dried (Na2SO4), and concentrated to yield (1-formylcyclopropyl)carbamic acid tert-butyl ester as a colorless oil (393 mg) which was used immediately in the next step without further purification.

Workup

  1. customquenched with 6 mL of a solution of KHSO4 in water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with Et2O
  4. washThe combined organic layers were washed with 1 N HCl, saturated NaHCO3, and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ed28b095e9f0473a8db938b51ecebd08
Source dataset
uspto-grants-2011_09
Patent number
US08013183B2

Reaction notes

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