Ethanol → (R)-(-)-alpha-(1-Aziridinylmethyl)-2-nitro-1H-imidazole-1-ethanol

HRID 266718Notes

Reaction equation

HRID 266718 reaction equation
[N+:1]([C:4]1[N:5]([CH2:9][C@H:10]2[CH2:12][O:11]2)[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].C(O)C.C([N:18]([CH2:21][CH3:22])CC)C>>[N:18]1([CH2:12][C@@H:10]([OH:11])[CH2:9][N:5]2[CH:6]=[CH:7][N:8]=[C:4]2[N+:1]([O-:3])=[O:2])[CH2:21][CH2:22]1

Participants

4

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 11768967(S)-(-)-2-Nitro-1-(2-oxiranylmethyl)-1H-imidazole

Product 1

HCID 10242276(R)-(-)-alpha-(1-Aziridinylmethyl)-2-nitro-1H-imidazole-1-ethanol

Procedure

A solution of 0.3 g (1.8 mmole) of (S)-(-)-2-nitro-1-(2-oxiranyl-methyl)-1H-imidazole, 0.24 g (5.4 mmole) of 1H-aziridine, and 3.5 mL of 99:1 absolute ethanol:triethylamine is heated at reflux for 10 minutes, cooled, and concentrated. The residue is crystallized from 99:1 absolute ethanol:triethylamine to give product, mp 119.5°-121° C. [α]D25 =-28.7° [c1.15, chloroform].

Workup

  1. temperatureat reflux for 10 minutes
  2. temperaturecooled
  3. concentrationconcentrated
  4. customThe residue is crystallized from 99:1 absolute ethanol
  5. customtriethylamine to give product, mp 119.5°-121° C. [α]D25 =-28.7° [c1.15, chloroform]

Sources & evidence

ORD record
ord-cfcb45190b8744ca8553b1e4ea1754a8
Source dataset
uspto-grants-1997_07
Patent number
US05652255

Reaction notes

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