HCID 178516313, compound → HCID 178516315, compound

HRID 1788097Notes

Reaction equation

HRID 1788097 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([CH2:19][C:18]4[C:14]5[N:15]=[N:16][NH:17][C:13]=5[CH:12]=[CH:11][C:10]=4[C:9]=13)[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([CH2:19][C:18]4[C:14]5[N:15]=[N:16][NH:17][C:13]=5[CH:12]=[CH:11][C:10]=4[C:9]=13)[CH2:7][CH2:6]2

Participants

3

Reactant 1

HCID 178516313HCID 178516313, compound

Product 1

HCID 178516315HCID 178516315, compound

Reagents, catalysts & solvents 1

HCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

6-(trifluoromethyl)-3,9,10,11-tetrahydro-8,10a-methanocyclohepta-[1,2]indeno[4,5-d][1,2,3]triazol-7(8H)-one [1.8 g, (8R,10aS): (8S,10aR) enantiomeric ratio ˜2:1] was dissolved in 1/1 ethanol/methanol (130 mL) and resolved by chiral HPLC on a 2.0×25 cm Daicel Chiralcel OJ column (4 mL injections, elution with 35% EtOH:Heptane at 7.5 mL/min, fractions monitored at 310 nm). The pure fractions containing the first enantiomer to elute (enantiomer A) were combined and concentrated to give (8R,10aS)-6-(trifluoromethyl)-3,9,10,11-tetrahydro-8,10a-methanocyclohepta[1,2]indeno[4,5-d][1,2,3]triazol-7(8H)-one as a white solid which had a negative rotation. The fractions containing the second enantiomer to elute (enantiomer B) were combined and concentrated to give(8S,10aR)-6-(trifluoromethyl)-3,9,10,11-tetrahydro-8,10a-methanocyclohepta[1,2]indeno[4,5-d][1,2,3]triazol-7(8H)- one as a solid which had a positive rotation.

Workup

  1. washresolved by chiral HPLC on a 2.0×25 cm Daicel Chiralcel OJ column (4 mL injections, elution with 35% EtOH:Heptane at 7.5 mL/min, fractions monitored at 310 nm)
  2. additionThe pure fractions containing the first enantiomer
  3. washto elute (enantiomer A)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ee17a8ee917b4310acf2748350a329c2
Source dataset
uspto-grants-2009_03
Patent number
US07511152B2

Reaction notes

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