Hydrochloric Acid → racemic (1S,2R)-ethyl 1-amino-2-methylcyclopropanecarboxylate hydrochloride

HRID 1772353Notes

Reaction equation

HRID 1772353 reaction equation
C1(C(=[N:14][C:15]2([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:17][CH:16]2[CH3:18])C2C=CC=CC=2)C=CC=CC=1.[ClH:24]>CCOCC>[ClH:24].[NH2:14][C:15]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:17][CH:16]1[CH3:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 123951729racemic (1S,2R)-ethyl 1-((diphenylmethylene)amino)-2-methylcyclopropanecarboxylate

Product 1

HCID 131734666racemic (1S,2R)-ethyl 1-amino-2-methylcyclopropanecarboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A round bottomed flask was charged with racemic (1S,2R)-ethyl 1-((diphenylmethylene)amino)-2-methylcyclopropanecarboxylate and a stir bar. Et2O (50 mL, 0.5 M) was added, and the mixture was cooled to 0° C. for the addition of 1 N HCl (9 mL, 1.2 equiv). The solution was warmed to room temperature and stirred overnight. The mixture was separated, and the organic layer was washed twice with water before being dried with Na2SO4 and concentrated. Lyophilization yielded racemic (1S,2R)-ethyl 1-amino-2-methylcyclopropanecarboxylate hydrochloride as a colorless oil that solidified upon sitting (yield not determined). LRMS (M+H)+: 144 m/z.

Workup

  1. customThe mixture was separated
  2. washthe organic layer was washed twice with water
  3. dry with materialbefore being dried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-63d6b6e163bd43b3900e8aa4b45dfab4
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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