1,4-Dioxane → HCID 86728494, compound

HRID 1472632Notes

Reaction equation

HRID 1472632 reaction equation
[Br-:1].[C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][NH+:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H].O1CCOC[CH2:17]1>>[Br-:1].[CH3:17][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[NH+:9]=1

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 86728495HCID 86728495, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86728494HCID 86728494, compound

Conditions

Temperature
100 °C

Procedure

To a 100 ml stainless steel autoclave, 21.9 mg (0.0125 mmol) of [{IrH((S)-SEGPHOS)}2(μ-Cl)3]Cl and 63 mg (0.25 mmol) of 2-phenylpyridinium bromide were added, and the autoclave was pruged with argon. Then, 3.0 ml of dioxane was added thereto. Subsequently, hydrogen was introduced at a pressure of 1.0 MPa, followed by stirring at 100° C. for 20 hours. After cooloing, the reaction product was analyzed by NMR and HPLC. The conversion was 91%, and the enantiomeric excess was 67% ee.

Sources & evidence

ORD record
ord-962d2da104634c8eb26eb606a1c1d4f9
Source dataset
uspto-grants-2015_04
Patent number
US09012649B2

Reaction notes

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