(+/-)-3-Methyl-5'-nitro-spiro[imidazolidine-4,2'-indane]-2,5-dione → (R)-3-Methyl-5'-nitro-spiro[imidazolidine-4,2'-indane]-2,5-dione

HRID 656365Notes

Reaction equation

HRID 656365 reaction equation
[CH3:1][N:2]1[C:6]2([CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=3)[CH2:7]2)[C:5](=[O:18])[NH:4][C:3]1=[O:19]>CO.CC#N.C(NCC)C>[CH3:1][N:2]1[C@:6]2([CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=3)[CH2:7]2)[C:5](=[O:18])[NH:4][C:3]1=[O:19]

Participants

5

Reactant 1

HCID 18440305(+/-)-3-Methyl-5'-nitro-spiro[imidazolidine-4,2'-indane]-2,5-dione2×

Product 1

HCID 67016436(R)-3-Methyl-5'-nitro-spiro[imidazolidine-4,2'-indane]-2,5-dione

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 8021DiethylamineSolvent

Procedure

(±)-3-Methyl-5′-nitro-spiro[imidazolidine-4,2′-indane]-2,5-dione (described in Intermediate 7) was dissolved in a mixture of MeOH, CH3CN and diethylamine and the enantiomers were resolved by HPLC, utilizing a ChiralPak AD column and eluting with CH3CN:MeOH—90:10. The first major peak to elute was (S)-3-methyl-5′-nitro-spiro[imidazolidine-4,2′-indane]-2,5-dione and the second major peak to elute was (R)-3-methyl-5′-nitro-spiro[imidazolidine-4,2′-indane]-2,5-dione, the title compound. MS: m/z=262 (M+1).

Workup

  1. washeluting with CH3CN
  2. washThe first major peak to elute
  3. washthe second major peak to elute

Sources & evidence

ORD record
ord-eefea47c46d74b1fac48dfd64c777370
Source dataset
uspto-grants-2011_12
Patent number
US08071770B2

Reaction notes

Loading…