1-Octanol → HCID 67917358, compound

HRID 1886332Notes

Reaction equation

HRID 1886332 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([OH:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH:14]12[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]1)[C@@H:16]([C:22](O)=[O:23])[NH:15]2.CCOCC>O.CCOCC>[ClH:3].[CH2:5]([O:13][C:22]([C@@H:16]1[CH:17]2[CH2:20][CH2:21][CH:14]([CH2:19][CH2:18]2)[NH:15]1)=[O:23])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 9571-OctanolHCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 10866570(3S)-2-Azabicyclo[2.2.2]octane-3-carboxylic acid

Product 1

HCID 67917358HCID 67917358, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 21584184Diethylether waterSolvent

Conditions

Temperature
0 °C

Procedure

9.6 ml of thionyl chloride are added dropwise into a 250 ml round-bottomed flask containing 60 ml of n-octanol cooled to 0° C. After stirring for 10 min at 0° C., 18.6 g of (3S)-2-azabicyclo[2.2.2]octane-3-carboxylic acid (described in Patent FR 2,585,709) are added slowly. The reaction mixture is left stirring overnight at room temperature, then heated for 6 hours at 80° C. and again left overnight at room temperature. After adding 100 ml of anhydrous ether and filtering off the unreacted hydrochloride, the filtrate is condensed and then taken up with a water/ether mixture (50:50). The expected product is obtained after concentration of the aqueous phase and then drying under vacuum.

Workup

  1. waitThe reaction mixture is left
  2. stirringstirring overnight at room temperature
  3. temperatureheated for 6 hours at 80° C. and again left overnight at room temperature
  4. filtrationfiltering off the unreacted hydrochloride
  5. customcondensed

Sources & evidence

ORD record
ord-f431ab1817e84c61a7bd674e6802d370
Source dataset
uspto-grants-1992_09
Patent number
US05151432

Reaction notes

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