Tetrahydrofuran → tert-Butyl (1S,2S)-1-amino-2-ethylcyclopropane-1-carboxylate

HRID 500336Notes

Reaction equation

HRID 500336 reaction equation
[C:1]([O:5][C:6]([C@:8]1([NH:13]C(OCC[Si](C)(C)C)=O)[CH2:10][C@@H:9]1[CH2:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>C(OCC)(=O)C>[C:1]([O:5][C:6]([C@:8]1([NH2:13])[CH2:10][C@@H:9]1[CH2:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 86601847(1S,2S) 2-Ethyl-1-(2trimethylsilanylethoxycarbonylamino)cyclopropane-carboxylic acid tert-butyl ester

Product 1

HCID 86620254tert-Butyl (1S,2S)-1-amino-2-ethylcyclopropane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To the product of Step 3 (3 g, 9 mmol) was added a 1.0M TBAF solution in THF (9.3 mL, 9.3 mmol). The mixture was heated to reflux for 1.5 hours, cooled to room temperature, and diluted with 500 mL of ethyl acetate. The solution was successively washed with water (2×100 mL) and brine (2×100 mL), dried (MgSO4), filtered, and concentrated in vacuo to provide the desired product.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. washThe solution was successively washed with water (2×100 mL) and brine (2×100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b1f5d14761324a30ac8a940d3aef1dfc
Source dataset
uspto-grants-2010_08
Patent number
US07772180B2

Reaction notes

Loading…