Potassium Carbonate → HCID 57722502, compound

HRID 1986624Notes

Reaction equation

HRID 1986624 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][NH:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:15][CH2:16][CH2:17][CH2:18]I.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][N:11]2[CH2:18][CH2:17][CH2:16][Cl:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 813631-Chloro-3-iodopropaneHCID 2760898(1S,4S)-tert-butyl 2,5-diazabicyclo(2.2.1)heptane-2-carboxylate

Product 1

HCID 57722502HCID 57722502, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.10 g, 0.50 mmol) in acetone (2 mL) was added 1-chloro-3-iodo-propane (0.10 g, 0.50 mmol, 1 eq) and K2CO3 (0.084 g, 0.60 mmol, 1.2 eq). The mixture was heated at 50° C. for 3 h and then cooled to r.t. The mixture was filtered through Celite and the filtrate was concentrated in vacuo. Chromatography on silica gel by eluting with 5% MeOH/CH2Cl2 gave 0.095 g (69%) of 5-(3-chloro-propyl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester as a yellowish oil. 1H NMR (300 MHz, CDCl3): δ 4.20 (m, 1H), 3.58 (m, 2H), 3.46 (m, 2H), 3.12 (m, 1H), 2.86 (m, 1H), 2.62 (m, 3H), 1.82 (m, 3H), 1.66 (m, 1H), 1.41 (s, 9H).

Workup

  1. temperaturecooled to r.t
  2. filtrationThe mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. washChromatography on silica gel by eluting with 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-a911aab4df2a4b1591603ae4edb0b3d9
Source dataset
uspto-grants-2009_06
Patent number
US07550467B2

Reaction notes

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