(3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1-((S,E)-1-(ethylsulfonyl)pent-1-en-3-yl)-3-methylpiperidin-2-one → (3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1-((S)-1-(ethylsulfonyl)pentan-3-yl)-3-methylpiperidin-2-one

HRID 1048465Notes

Reaction equation

HRID 1048465 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12]([C@@H:21]([CH2:29][CH3:30])/[CH:22]=[CH:23]/[S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])[C:11](=[O:31])[C@:10]([CH2:33][CH:34]3[CH2:38][O:37][C:36]([CH3:40])([CH3:39])[O:35]3)([CH3:32])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1>ClCCCl.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CC=CCCC=C1.C1C=CN=CC=1.F[P-](F)(F)(F)(F)F.[Ir]>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)[N:12]([C@@H:21]([CH2:29][CH3:30])[CH2:22][CH2:23][S:24]([CH2:27][CH3:28])(=[O:25])=[O:26])[C:11](=[O:31])[C@:10]([CH2:33][CH:34]3[CH2:38][O:37][C:36]([CH3:40])([CH3:39])[O:35]3)([CH3:32])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 58573273(3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1-((S,E)-1-(ethylsulfonyl)pent-1-en-3-yl)-3-methylpiperidin-2-one

Product 1

HCID 58573576(3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1-((S)-1-(ethylsulfonyl)pentan-3-yl)-3-methylpiperidin-2-one

Reagents, catalysts & solvents 2

HCID 5702647(1,5-Cyclooctadiene)pyridine(tricyclohexylphosphine)iridium hexafluorophosphateCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1-((S,E)-1-(ethylsulfonyl)pent-1-en-3-yl)-3-methylpiperidin-2-one (65.0 mg, 0.107 mmol; Example 205, Step B) in 1,2-dichloroethane (1.07 mL) at 25° C. was added Crabtree's catalyst (7.74 mg, 9.61 μmol). The reaction system (a hydrogenation bomb) was flushed with hydrogen gas 3×, pressurized with hydrogen at 3447.38 kilopascal, and the reaction was stirred at 25° C. for 24 hours. The reaction mixture was filtered through celite, washed with DCM, and concentrated under reduced pressure to yield the title compound as an off-white solid.

Workup

  1. customThe reaction system (a hydrogenation bomb) was flushed with hydrogen gas 3×
  2. filtrationThe reaction mixture was filtered through celite
  3. washwashed with DCM
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ed6af0a68b824169ab037f242cf04513
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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