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

HRID 1743044Notes

Reaction equation

HRID 1743044 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].[NH:13]1[CH2:15][CH2:14]1>C(Cl)(Cl)Cl>[N:13]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])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 9033AziridineHCID 11768967(S)-(-)-2-Nitro-1-(2-oxiranylmethyl)-1H-imidazole

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Reaction of (S)-(-)-2-nitro-1-(2-oxiranylmethyl)-1H-imidazole with 1H--aziridine as described in Example 1(e) gives the product, mp 119.5°-121° C. [α]D24 =-28.7° [c1.15, chloroform].

Sources & evidence

ORD record
ord-9e55db9c9f4745fbb9a234bf0c106227
Source dataset
uspto-grants-1994_08
Patent number
US05342959

Reaction notes

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