4-Toluenesulfonyl chloride → HCID 12297768, compound

HRID 1478554Notes

Reaction equation

HRID 1478554 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][OH:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17].CCN(CC)CC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:23][C:22]1[CH:24]=[CH:25][C:19]([S:16]([O:15][CH2:14][C@H:10]2[O:11][CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9]2)(=[O:18])=[O:17])=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 736507(S)-(4-benzylmorpholin-2-yl)methanol

Product 1

HCID 12297768HCID 12297768, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(S)-(4-benzylmorpholin-2-yl)methanol 36 g (173.68 mmnol) was dissolved in CH2Cl2 (400 ml), and TsCl (49.6 g, 260.52 mmol), DMAP (2.12 g, 17.36 mmol), and Et3N (36.31 ml, 260.52 mmol) were added, followed by stirring at room temperature for 1 hour. After the completion of the reaction, the reaction mixture was extracted with H2O and EA, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and then the residue was purified by column chromatography (EA:Hex=1:4), to give (S)-(4-benzylmorpholin-2-yl)methyl 4-methylbenzene sulfonate as a white solid (62.15 g, 99%).

Workup

  1. customAfter the completion of the reaction
  2. extractionthe reaction mixture was extracted with H2O and EA
  3. customby drying
  4. filtration(Na2SO4), filtration, and concentration under reduced pressure
  5. customthe residue was purified by column chromatography (EA:Hex=1:4)

Sources & evidence

ORD record
ord-c12d0f5272fe4398a44ff044570c6632
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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