(R)-Quinuclidin-3-yl ((S)-(3-(2-((4-(hydroxymethyl)phenyl)amino)-2-oxoethoxy)phenyl)(phenyl)methyl)carbamate → (R)-Quinuclidin-3-yl ((S)-(3-(2-((4-formylphenyl)amino)-2-oxoethoxy)phenyl)-(phenyl)methyl)carbamate

HRID 2205717Notes

Reaction equation

HRID 2205717 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:38])[CH2:11][O:12][C:13]2[CH:14]=[C:15]([C@@H:19]([NH:26][C:27](=[O:37])[O:28][C@@H:29]3[CH:34]4[CH2:35][CH2:36][N:31]([CH2:32][CH2:33]4)[CH2:30]3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=[CH:17][CH:18]=2)=[CH:5][CH:4]=1>O1CCOCC1.[O-2].[Mn+4].[O-2]>[CH:2]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:38])[CH2:11][O:12][C:13]2[CH:14]=[C:15]([C@@H:19]([NH:26][C:27](=[O:37])[O:28][C@@H:29]3[CH:34]4[CH2:33][CH2:32][N:31]([CH2:36][CH2:35]4)[CH2:30]3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=[CH:17][CH:18]=2)=[CH:7][CH:8]=1)=[O:1]

Participants

4

Reactant 1

HCID 90204880(R)-Quinuclidin-3-yl ((S)-(3-(2-((4-(hydroxymethyl)phenyl)amino)-2-oxoethoxy)phenyl)(phenyl)methyl)carbamate

Product 1

HCID 90211965(R)-Quinuclidin-3-yl ((S)-(3-(2-((4-formylphenyl)amino)-2-oxoethoxy)phenyl)-(phenyl)methyl)carbamate

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of (R)-quinuclidin-3-yl ((S)-(3-(2-((4-(hydroxymethyl)-phenyl)amino)-2-oxoethoxy)phenyl)(phenyl)methyl)carbamate (0.68 g, 1.31 mmol) in 1,4-dioxane (10 mL) was added manganese (IV) oxide (0.57 g, 6.58 mmol). The reaction mixture was stirred at room temperature for 60 hours. The suspension was filtered and the filter cake was washed with ethyl acetate. The filtrate was evaporated at reduced pressure to afford the crude title compound. This material was used without further purification.

Workup

  1. filtrationThe suspension was filtered
  2. washthe filter cake was washed with ethyl acetate
  3. customThe filtrate was evaporated at reduced pressure

Sources & evidence

ORD record
ord-9cca3271e79e4f3bad4d8854e40f27d6
Source dataset
uspto-grants-2016_06
Patent number
US09371318B2

Reaction notes

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