Potassium Carbonate → HCID 18540402, compound

HRID 1374124Notes

Reaction equation

HRID 1374124 reaction equation
[CH:1]12[O:9][CH:5]([CH2:6][NH:7][CH2:8]1)[CH2:4][N:3]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:2]2.Cl[CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1.BrBr.C([O-])([O-])=O.[K+].[K+]>>[N:25]1[CH:26]=[CH:27][C:22]([CH2:21][CH2:20][CH2:19][CH2:18][N:7]2[CH2:6][CH:5]3[O:9][CH:1]([CH2:2][N:3]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4]3)[CH2:8]2)=[CH:23][CH:24]=1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 24408BromineHCID 109539414-(4-Chlorobutyl)pyridineHCID 185404123-Boc-9-oxa-3,7-diazabicyclo[3.3.1]nonane

Product 1

HCID 18540402HCID 18540402, compoundYield 45.5%

Procedure

tert-Butyl 9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (1.35 g, 5.9 mmol, see Preparation A and Preparation C(iii) above) was mixed with 4-(4-chlorobutyl)pyridine (1.35 g, 7.37 mmol, see Example 10(i) above), Br2 (0.094 g, 0.59 mmol ) and K2CO3 (3.26 g, 23.6 mmol). The mixture was refluxed under argon for 3 days. The reaction mixture was filtered, evaporated and purified by chromatography (DCM, 2–5% MeOH) giving 0.97 g (44%) of the sub-title compound.

Workup

  1. temperatureThe mixture was refluxed under argon for 3 days
  2. filtrationThe reaction mixture was filtered
  3. customevaporated
  4. custompurified by chromatography (DCM, 2–5% MeOH)

Sources & evidence

ORD record
ord-a2df278ac4e24e4aaf7ce09aee22f1d3
Source dataset
uspto-grants-2007_01
Patent number
US07164017B2

Reaction notes

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