4-Toluenesulfonyl chloride → HCID 86732633, compound

HRID 626392Notes

Reaction equation

HRID 626392 reaction equation
[O:1]1[CH2:4][CH2:3][C@@H:2]1[CH2:5][CH2:6][OH:7].[S:8](Cl)([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)(=[O:10])=[O:9]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:15][C:14]1[CH:16]=[CH:17][C:11]([S:8]([O:7][CH2:6][CH2:5][C@H:2]2[CH2:3][CH2:4][O:1]2)(=[O:10])=[O:9])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 89304729HCID 89304729, compound

Product 1

HCID 86732633HCID 86732633, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The mixture of (S)-2-(oxetan-2-yl)ethanol (408 mg, 4 mmol), TsCl (1.15 g, 6 mmol), TEA (0.85 g, 6 mmol) and DMAP (92 mg, 0.8 mmol) in DCM (20 mL) was stirred at RT for 18 h. Then the mixture was concentrated, the residue was dissolved into EtOAc (15 mL), washed with sat. NaHCO3 aqueous solution, water and brine, then the EtOAc layers was dried with Na2SO4, then the solvent was removed under the reduced pressure. The crude product was purified with Combiflash (PE/EtOAc=5/1, silica gel) to give the titled compound.

Workup

  1. concentrationThen the mixture was concentrated
  2. dissolutionthe residue was dissolved into EtOAc (15 mL)
  3. washwashed with sat. NaHCO3 aqueous solution, water and brine
  4. dry with materialthe EtOAc layers was dried with Na2SO4
  5. customthe solvent was removed under the reduced pressure
  6. customThe crude product was purified with Combiflash (PE/EtOAc=5/1, silica gel)

Sources & evidence

ORD record
ord-3fc4b1bbecee437bafd54cb3c481c398
Source dataset
uspto-grants-2016_04
Patent number
US09309227B2

Reaction notes

Loading…