HCID 67175440, compound → HCID 67495575, compound

HRID 1913089Notes

Reaction equation

HRID 1913089 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([N:13]3[CH:18]4[CH2:19][CH2:20][CH:14]3[CH:15]=[C:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17]4)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1>CO.[H][H].O=[Pt]=O>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([N:13]3[CH:18]4[CH2:19][CH2:20][CH:14]3[CH2:15][CH:16]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:17]4)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 67175440HCID 67175440, compound

Product 1

HCID 67495575HCID 67495575, compound

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

PtO2 (40 mg) is added to a solution of (2,3-dihydro-benzo[1,4]dioxin-6-yl)-(3-phenyl-8-aza-bicyclo[3.2.1]oct-2-en-8-yl)-methanone (0.40 g) in methanol (5 mL). The resulting mixture is shaken in hydrogen atmosphere (1 bar) at room temperature for 6 h. Then, the mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→9:1) to give the title product as a ca. 1:1 mixture of endo and exo isomer.

Workup

  1. filtrationThen, the mixture is filtered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→9:1)

Sources & evidence

ORD record
ord-c476f69a50834b8a8be645962aeea4c4
Source dataset
uspto-grants-2013_12
Patent number
US08609690B2

Reaction notes

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