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

HRID 2261710Notes

Reaction equation

HRID 2261710 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>CCOC(C)=O>[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 EtOAc was cooled to 8° C. using an ice bath and a solution of 2.17 g (21.0 mmol) of sulfuric acid in 4.0 mL of EtOAc was added in 5 min. The ice bath was removed and the reaction mixture was stirred for 30 min at RT and 1 h at 50° C. The reaction mixture was then cooled to RT and used in the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-fd6191a2a5d74840bc9ed4566559e69b
Source dataset
uspto-grants-2010_12
Patent number
US07847106B2

Reaction notes

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