Racemic (7R,8R,10aS)-6-chloro-3,7,8,9,10,11-hexahydro-8,10a-methanoazuleno-[2,1-e]indazol-7-ol → (Rac)-(7r,8r,10as)-6-chloro-3,7,8,9,10,11-hexahydro-8,10a-methanoazuleno-[2,1-e]indazol-7-ol
Reaction equation
[Cl:1][C:2]1[CH:3]([OH:20])[CH:4]2[CH2:19][C:7]3([C:18]=1[C:17]1[CH:16]=[CH:15][C:14]4[NH:13][N:12]=[CH:11][C:10]=4[C:9]=1[CH2:8]3)[CH2:6][CH2:5]2>C(O)C.CO>[Cl:1][C:2]1[C@H:3]([OH:20])[C@H:4]2[CH2:19][C@@:7]3([C:18]=1[C:17]1[CH:16]=[CH:15][C:14]4[NH:13][N:12]=[CH:11][C:10]=4[C:9]=1[CH2:8]3)[CH2:6][CH2:5]2Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Racemic (7R,8R,10aS)-6-chloro-3,7,8,9,10,11-hexahydro-8,10a-methanoazuleno-[2,1-e]indazol-7-ol (318 mg) was dissolved in 4/1 ethanol/methanol (25 mL) and resolved by chiral HPLC on a 2.0×25 cm Daicel Chiralcel OJ column (3-4 mL injections, elution with 35% EtOH:Heptane at 7.5 mL/min, fractions monitored at 254 nm). The fractions containing the first enantiomer to elute (enantiomer A) were combined and concentrated to a clear oil which had a negative rotation. The pure fractions containing the second enantiomer to elute (enantiomer B) were combined, concentrated, and lyophilized from benzene to give a white solid which had a positive rotation.
Workup
- washresolved by chiral HPLC on a 2.0×25 cm Daicel Chiralcel OJ column (3-4 mL injections, elution with 35% EtOH:Heptane at 7.5 mL/min, fractions monitored at 254 nm)
- additionThe fractions containing the first enantiomer
- washto elute (enantiomer A)
- concentrationconcentrated to a clear oil which
- additionThe pure fractions containing the second enantiomer
- washto elute (enantiomer B)
- concentrationconcentrated
- customto give a white solid which
Sources & evidence
- ORD record
- ord-c1ecd8a3e4a542968facdda565510cc2
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07923568B2
Reaction notes
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