Sulfuric Acid → rac-ethyl (1R,2S)-1-amino-2-ethenylcyclopropane-1-carboxylate

HRID 604809Notes

Reaction equation

HRID 604809 reaction equation
[CH2:1]([O:3][C:4]([C@@:6]1([NH:11]C(OC(C)(C)C)=O)[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].S(=O)(=O)(O)O>C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C@@:6]1([NH2:11])[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 10658673Ethyl (1R,2S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethenylcyclopropanecarboxylate

Product 1

HCID 10820795rac-ethyl (1R,2S)-1-amino-2-ethenylcyclopropane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
8 °C

Procedure

A suspension of 5.11 g (20.0 mmol) of (1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid ethyl ester (commercially available from Synthetech Oregon, USA) in 1.94 mL of ethyl acetate was cooled to 8° C. using an ice bath. Then a solution of 2.17 g (21.0 mmol) of sulfuric acid in 4.0 mL of ethyl acetate was added in 5 min. The ice bath was removed and the reaction mixture was stirred for 30 min at room temperature and 1 h at 50° C. The reaction mixture was then cooled to room temperature and used in the next step without further purification.

Workup

  1. customThe ice bath was removed
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. customused in the next step without further purification

Sources & evidence

ORD record
ord-5b44c30be31f4a6fb2d233d6ed607855
Source dataset
uspto-grants-2011_03
Patent number
US07910728B2

Reaction notes

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