4-Toluenesulfonyl chloride → HCID 59291457, compound

HRID 383942Notes

Reaction equation

HRID 383942 reaction equation
[OH:1][C:2]1([CH2:14][CH2:15][OH:16])[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[OH:1][C:2]1([CH2:14][CH2:15][O:16][S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)(=[O:25])=[O:24])[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[CH2:3]1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 59291400HCID 59291400, compound

Product 1

HCID 59291457HCID 59291457, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under cooling with a cryogen (−10° C. to 0° C.), to a solution of tert-butyl 3-hydroxy-3-(2-hydroxyethyl)pyrrolidine-1-carboxylate (4.72 g) in pyridine (10 mL) was added p-toluene sulfonylchloride (1.68 g), followed by stirring at room temperature for overnight. The reaction mixture was concentrated under reduced pressure, and 1 M hydrochloric acid was added thereto, followed by extraction with EtOAc. The organic layer was washed with water and brine in this order, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane: EtOAc) to obtain tert-butyl 3-hydroxy-3-(2-{[(4-methylphenyl)sulfonyl]oxy}ethyl)pyrrolidine-1-carboxylate (3.25 g) as a colorless oily substance.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and 1 M hydrochloric acid
  2. additionwas added
  3. extractionfollowed by extraction with EtOAc
  4. washThe organic layer was washed with water and brine in this order
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane: EtOAc)

Sources & evidence

ORD record
ord-82fb32e2b86d4ae29b59a774edbdd9ae
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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