Ethyl Acetate → N-nitroso-N-(tert-butoxycarbonyl)amino-cyclopropane

HRID 1522528Notes

Reaction equation

HRID 1522528 reaction equation
F[B-](F)(F)F.[N:6]#[O+:7].[CH:8]1([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:10][CH2:9]1.CCOC(C)=O>N1C=CC=CC=1.C(#N)C>[CH:8]1([N:11]([N:6]=[O:7])[C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 11137142Nitrilooxonium tetrafluoroborateHCID 15698228tert-Butyl N-cyclopropylcarbamate

Product 1

HCID 57941319N-nitroso-N-(tert-butoxycarbonyl)amino-cyclopropane

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
-30 °C

Procedure

Nitrosonium tetrafluoroborate (2.415 g, 20.67 mmol) was added in several portions to a cooled (−30° C.) solution of 1,1-dimethylethyl cyclopropylcarbamate (2.5 g, 15.90 mmol) in anhydrous Pyridine (4 mL) and Acetonitrile (40 mL). The solution was stirred at −30° C. for 30 minutes then at 0° C. for 2 hours. Ice water and EtOAc were added. The organic phase was separated and washed with 1N HCl, 1N NaHCO3, brine, dried over MgSO4, filtered and concentrated in vacuo. The product was collected as 2.66 g. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.37-0.79 (m, 4 H), 1.64 (s, 9 H), 2.18-2.41 (m, 1 H).

Workup

  1. waitat 0° C. for 2 hours
  2. customThe organic phase was separated
  3. washwashed with 1N HCl, 1N NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was collected as 2.66 g

Sources & evidence

ORD record
ord-9ae6c48b1b3e4cae9422f1da1acbfb6b
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

Loading…