4-Toluenesulfonyl chloride → 1-Tosyl-3-pyrrolidinol Tosylate

HRID 1742700Notes

Reaction equation

HRID 1742700 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH:13]1[CH2:17][CH2:16][NH:15][CH2:14]1>N1C=CC=CC=1>[S:7]([N:15]1[CH2:16][CH2:17][CH:13]([O:12][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:14]1)([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 982104-Hydroxypyrrolidine

Product 1

HCID 150203551-Tosyl-3-pyrrolidinol Tosylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Para-toluenesulphonyl chloride (68.8 g) was added, in portions, to a solution of 3-(R,S)-hydroxypyrrolidine (15 g) in dry pyridine (200 ml) at 0° C. The mixture was allowed to warm to room temperature and stirred for 16 hours. The solution was concentrated in vacuo to approximately half the original volume then partitioned between dichloromethane (500 ml) and water (300 ml). The layers were separated and the aqueous layer was extracted with dichloromethane (3×100 ml). The combined dichloromethane extracts were washed with 2M hydrochloric acid (100 ml) and 10% aqueous sodium hydroxide (100 ml) then dried (MgSO4) and concentrated in vacuo to give an oil which was crystallised from dichloromethane/ether to give the title compound as a microcrystalline powder, yield 28.3 g, m.p. 119°-121° C.

Workup

  1. concentrationThe solution was concentrated in vacuo to approximately half the original volume
  2. customthen partitioned between dichloromethane (500 ml) and water (300 ml)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (3×100 ml)
  5. washThe combined dichloromethane extracts were washed with 2M hydrochloric acid (100 ml) and 10% aqueous sodium hydroxide (100 ml)
  6. dry with materialthen dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give an oil which
  9. customwas crystallised from dichloromethane/ether

Sources & evidence

ORD record
ord-be33791ca2f545c6ba2379366e86d700
Source dataset
uspto-grants-1994_08
Patent number
US05340831

Reaction notes

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