(R)-Quinuclidin-3-yl ((S)-(3-(2-((3-(hydroxymethyl)phenyl)amino)-2-oxoethoxy)phenyl)(phenyl)methyl)carbamate → (R)-Quinuclidin-3-yl ((S)-(3-(2-((3-formylphenyl)amino)-2-oxoethoxy)phenyl)-(phenyl)methyl)carbamate

HRID 874839Notes

Reaction equation

HRID 874839 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:38])[NH:11][C@H:12]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][C:27]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][OH:37])[CH:31]=3)=[O:28])[CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:2]2>O1CCOCC1.[O-2].[Mn+4].[O-2]>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:38])[NH:11][C@H:12]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][C:27]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH:36]=[O:37])[CH:31]=3)=[O:28])[CH:20]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:2]2

Participants

4

Reactant 1

HCID 90203069(R)-Quinuclidin-3-yl ((S)-(3-(2-((3-(hydroxymethyl)phenyl)amino)-2-oxoethoxy)phenyl)(phenyl)methyl)carbamate

Product 1

HCID 90210011(R)-Quinuclidin-3-yl ((S)-(3-(2-((3-formylphenyl)amino)-2-oxoethoxy)phenyl)-(phenyl)methyl)carbamate

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl((S)-(3-(2-((3-(hydroxymethyl)-phenyl)amino)-2-oxoethoxy)phenyl)(phenyl)methyl)carbamate (0.35 g, 0.68 mmol) in 1,4-dioxane (25 mL) was added manganese (IV) oxide (0.58 g, 6.8 mmol) and the reaction mixture stirred at room temperature for 2 hours and then at 50° C. for 15 hours. The suspension was filtered through a pad of celite. The solvent was evaporated at reduced pressure to afford the crude material. This material was used in the next step without further purification.

Workup

  1. waitat 50° C. for 15 hours
  2. filtrationThe suspension was filtered through a pad of celite
  3. customThe solvent was evaporated at reduced pressure

Sources & evidence

ORD record
ord-20685a0eac764c76a6ab8e2775021a1d
Source dataset
uspto-grants-2015_03
Patent number
US08980913B2

Reaction notes

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