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

HRID 734238Notes

Reaction equation

HRID 734238 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) and the mixture heated to reflux for 1.5 hours, cooled to room temperature and then diluted with 500 mL of ethyl acetate. The solution was successively washed with water (2×100 mL), brine (2×100 mL), dried (MgSO4), filtered, and concentrated in vacuo to provide the title intermediate.

Workup

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

Sources & evidence

ORD record
ord-d73fd78c138a44a8982385aa0f1ee60f
Source dataset
uspto-grants-2009_09
Patent number
US07592336B2

Reaction notes

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