HCID 59397216, compound → HCID 24996754, compound

HRID 2076367Notes

Reaction equation

HRID 2076367 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[C:4](=[O:21])[CH:5]2[CH2:20][C:8]3([C:19]=1[C:18]1[CH:17]=[CH:16][C:15]4[NH:14][N:13]=[CH:12][C:11]=4[C:10]=1[CH2:9]3)[CH2:7][CH2:6]2>C(O)C.CO>[F:22][C:2]([F:1])([F:23])[C:3]1[C:4](=[O:21])[C@H:5]2[CH2:20][C@@:8]3([C:19]=1[C:18]1[CH:17]=[CH:16][C:15]4[NH:14][N:13]=[CH:12][C:11]=4[C:10]=1[CH2:9]3)[CH2:7][CH2:6]2

Participants

3

Reactant 1

HCID 59397216HCID 59397216, compound

Product 1

HCID 24996754HCID 24996754, compound

Reagents, catalysts & solvents 1

HCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

Racemic (8R,10aS)-6-(trifluoromethyl)-3,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one (260 mg) was dissolved in ˜4/1 ethanol/methanol and resolved by chiral HPLC on a 2.0×25 cm Daicel Chiralcel OJ column (elution with 25% EtOH:Heptane at 7.5 mL/min, fractions monitored at 340 nm). The fractions containing the first enantiomer to elute (enantiomer A) were combined and concentrated to a clear oil which had a positive rotation. The pure fractions containing the second enantiomer to elute (enantiomer B) were combined, concentrated, and lyophilized from benzene to give (8R,10aS)-6-(trifluoromethyl)-3,9,10,11-tetrahydro-8,10a -methanoazuleno[2,1-e]indazol-7(8H)-one as a white solid which had a negative rotation.

Workup

  1. washresolved by chiral HPLC on a 2.0×25 cm Daicel Chiralcel OJ column (elution with 25% EtOH:Heptane at 7.5 mL/min, fractions monitored at 340 nm)
  2. additionThe fractions containing the first enantiomer
  3. washto elute (enantiomer A)
  4. concentrationconcentrated to a clear oil which
  5. additionThe pure fractions containing the second enantiomer
  6. washto elute (enantiomer B)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-99022c5b97664c63b36eae82c1996f6a
Source dataset
uspto-grants-2011_04
Patent number
US07923568B2

Reaction notes

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