Triethylamine → HCID 10314651, compound

HRID 1461110Notes

Reaction equation

HRID 1461110 reaction equation
C(N(CC)CC)C.[C:8]1([CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:15]2[CH2:18][C@@H:17]([OH:19])[C@@H:16]2[CH3:20])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[S:27](Cl)([CH3:30])(=[O:29])=[O:28]>ClCCl>[C:21]1([CH:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:15]2[CH2:18][C@@H:17]([O:19][S:27]([CH3:30])(=[O:29])=[O:28])[C@@H:16]2[CH3:20])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10243988(2s,3r)-1-(Diphenylmethyl)-2-methylazetidin-3-ol

Product 1

HCID 10314651HCID 10314651, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

50 g (0.495 mol) of triethylamine are added to a solution of 77.33 g (0.329 mol) of trans-1-diphenylmethyl-3-hydroxy-2-methylazetidine in 600 ml of dichloromethane and the mixture is cooled to 0° C. The temperature is maintained, a solution of 50 g (0.437 mol) of mesyl chloride is added dropwise and the mixture is left for 24 hours at room temperature. The resulting solution is washed twice with water (300 ml), dried with anhydrous sodium sulphate and evaporated, and an oil is obtained which, when crystallized with petroleum ether, gives 104.6 g (96%) of trans-1-diphenylmethyl-2-methyl-3-methylsulphonyloxyazetidine, melting point 68°-71° C.

Workup

  1. temperatureThe temperature is maintained
  2. washThe resulting solution is washed twice with water (300 ml)
  3. dry with materialdried with anhydrous sodium sulphate
  4. customevaporated
  5. customan oil is obtained which, when
  6. customcrystallized with petroleum ether

Sources & evidence

ORD record
ord-c86f601ae1534bf8bacff27b9153403b
Source dataset
uspto-grants-1991_12
Patent number
US05073646

Reaction notes

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