Hydrochloric Acid → HCID 20377405, compound

HRID 2052351Notes

Reaction equation

HRID 2052351 reaction equation
B#B.[C:3]([N:22]1[CH2:25][CH:24]([OH:26])[CH2:23]1)(=O)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[ClH:27]>O1CCCC1>[ClH:27].[CH2:3]([N:22]1[CH2:25][CH:24]([OH:26])[CH2:23]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6328200DiboronHCID 20377403HCID 20377403, compound

Product 1

HCID 20377405HCID 20377405, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 85 ml of 0.98 M diborane in tetrahydrofuran, maintained at about 10° C. under a nitrogen atomosphere, add a solution of 8.16 g 1-octadecanoyl-3-hydroxyazetidine in 420 ml dry tetrahydrofuran over a period of 1.5 hours. Stir for one hour at room temperature then heat for 1.5 hours at 55°-60° C. Allow the reaction mixture to cool to room temperature and cautiously acidify with 30 ml 6 M aqueous hydrochloric acid. Reflux for one hour and distill in vacuo until about 150 ml solvent is removed. Dilute the residue with 450 ml water and basify with 20 ml 50% aqueous sodium hydroxide. Extract three times with 150 ml portions of ethyl ether, dry the combined ethereal extracts over anhydrous sodium sulfate, and strip off solvent in vacuo. Dissolve the residue in 150 ml ethanol containing 12 ml 1.9 M ethereal hydrochloric acid and reflux under nitrogen for 0.5 hour. Remove the solvent in vacuo and triturate the residue with 280 ml ethyl ether to obtain 1-octadecyl-3-hydroxyazetidine hydrochloride, m.p. 108.5°-115° C. Stir this hydrochloride salt with 120 ml water, 10 ml 2.5 M sodium hydroxide and 40 ml methylene chloride for one hour. Separate the layers and extract the aqueous layer three times with 100 ml portions of methylene chloride. Combine the organic layer and extracts, dry over anhydrous sodium sulfate and remove the solvents in vacuo to obtain 1-octadecyl-3-hydroxyazetidine, m.p. 75.5°-78° C.

Workup

  1. temperaturethen heat for 1.5 hours at 55°-60° C
  2. temperatureto cool to room temperature
  3. temperatureReflux for one hour
  4. distillationdistill in vacuo until about 150 ml solvent
  5. customis removed
  6. additionDilute the residue with 450 ml water
  7. extractionExtract three times with 150 ml portions of ethyl ether
  8. dry with materialdry the combined ethereal extracts over anhydrous sodium sulfate, and strip off solvent in vacuo
  9. dissolutionDissolve the residue in 150 ml ethanol containing 12 ml 1.9 M ethereal hydrochloric acid
  10. temperaturereflux under nitrogen for 0.5 hour
  11. customRemove the solvent in vacuo
  12. customtriturate the residue with 280 ml ethyl ether

Sources & evidence

ORD record
ord-30644b3df4494e939d7e97570e7d6fca
Source dataset
uspto-grants-1980_01
Patent number
US04183923

Reaction notes

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