4-Toluenesulfonyl chloride → HCID 86729487, compound

HRID 712442Notes

Reaction equation

HRID 712442 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([CH2:13]O)[CH:10]([CH2:15][CH2:16][OH:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH2:1]([N:8]1[CH2:9][CH:10]2[CH2:15][CH2:16][O:17][CH2:13][CH:11]2[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 86729486HCID 86729486, compound

Product 1

HCID 86729487HCID 86729487, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 2-(1-benzyl-4-(hydroxymethyl)pyrrolidin-3-yl) ethanol (0.50 g) in toluene (30 mL) was added Et3N (0.8 mL), TsCl (0.75 g) and DMAP (10 mg). The mixture was stirred for 12 h at room temperature under N2, washed with water, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was used for the next step. To a solution of the above product in toluene (20 mL) was added Et3N (0.85 mL). The reaction mixture was heated to reflux for 4 h and cooled to room temperature. The reaction mixture was washed with water followed by brine. The mixture was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/CH3OH) to give the title compound (0.18 g, 13.61%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 218.3 (M+1).

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. additionTo a solution of the above product in toluene (20 mL) was added Et3N (0.85 mL)
  6. temperatureThe reaction mixture was heated
  7. temperatureto reflux for 4 h
  8. temperaturecooled to room temperature
  9. washThe reaction mixture was washed with water
  10. dry with materialThe mixture was dried over anhydrous Na2SO4
  11. concentrationconcentrated in vacuo
  12. customThe residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/CH3OH)

Sources & evidence

ORD record
ord-931150dd0cee472e99461d9e150f145b
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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