HCID 69523277, compound → HCID 69134265, compound

HRID 969506Notes

Reaction equation

HRID 969506 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]([C:5]1[C:6]2[CH2:7][CH2:8][CH2:9][O:10][C:11]=2[C:12]2[N:16]=[C:15]([C:17]3C=CC=C(C)C=3C)[NH:14][C:13]=2[CH:25]=1)=[O:4].C[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].[CH2:34](O)C.C(NCC)C>>[CH3:1][N:2]([CH3:26])[C:3]([C:5]1[C:6]2[CH2:7][CH2:8][C@H:9]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[O:10][C:11]=2[C:12]2[N:16]=[C:15]([CH3:17])[N:14]([CH3:34])[C:13]=2[CH:25]=1)=[O:4]

Participants

3

Reactant 2

HCID 69523277HCID 69523277, compoundHCID 87206544HCID 87206544, compound

Product 1

HCID 69134265HCID 69134265, compound

Procedure

Resolution of racemic 2,3-dimethylphenyl-3,6,7,8-tetrahydro-chromeno[7,8-d]imidazole-5-carboxylic acid dimethylamide (0.5 g, 1.4 mmol) was achieved by preparative chromatography using a 275×110 mm CHIRALPAK® AS-V 20 μm column. The mobile phase consisted of a n-heptan/ethanol/diethylamine mixture [95/5/0.1 (v/v/v)]. The separation was performed at room temperature with a flow rate of 1 ml/min. The products were detected at a wavelength of 225 nm. The separation afforded 0.19 g (39%; ee 99.8%) of the title compound ((8R)-enantiomer) as a white solid. m.p. 227°-228° C.

Workup

  1. customThe separation
  2. customwas performed at room temperature with a flow rate of 1 ml/min
  3. customThe separation

Sources & evidence

ORD record
ord-5bc88db57905409f8a790ac01b7a9e9a
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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