1,10-Phenanthroline → HCID 11809738, compound

HRID 1581752Notes

Reaction equation

HRID 1581752 reaction equation
[N:1]1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1.[I-].[I-].[Sm+2].[CH3:18][C@@H:19]1[C:24](=[O:25])[CH2:23][C@:22]2([CH:26]([CH3:28])[CH3:27])[C@H:20]1[CH2:21]2>C1COCC1>[OH:25][C@@:24]1([C:2]2[CH:3]=[CH:4][C:5]3[C:14](=[C:13]4[C:8](=[CH:7][CH:6]=3)[CH:9]=[CH:10][CH:11]=[N:12]4)[N:1]=2)[C@@H:19]([CH3:18])[C@@H:20]2[C@@:22]([CH:26]([CH3:28])[CH3:27])([CH2:21]2)[CH2:23]1

Participants

5

Reactant 3

HCID 13181,10-PhenanthrolineHCID 12304612HCID 12304612, compoundHCID 178506586HCID 178506586, compound

Product 1

HCID 11809738HCID 11809738, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Another embodiment of the process comprises mixing a solution of 1,10-phenanthroline in THF with a solution of samarium diiodide in THF and adding to the mixed solutions a solution of the chiral bicyclic ketone, (−)-thujone, in THF. The chiral product, 2-{(1S,3R,4S,5R)-(3-hydroxy-1-isopropyl-4-methylbicyclo[3.1.0]hex-3-yl)}-1,10-phenanthroline, is isolated and purified as described above in the preceding embodiment. This embodiment is illustrated by the following reaction scheme.

Sources & evidence

ORD record
ord-05ba32624bed417e8daa4befd93917ea
Source dataset
uspto-grants-2004_05
Patent number
US06730788B1

Reaction notes

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