4-Toluenesulfonyl chloride → 3(S)-azido-4-phenyl-1-(p-toluenesulphonyloxy)-2(S)-butanol

HRID 440111Notes

Reaction equation

HRID 440111 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.[N:12]([C@@H:15]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@H:16]([OH:19])[CH2:17][OH:18])=[N+:13]=[N-:14]>CN(C)C1C=CN=CC=1.ClCCl.N1C=CC=CC=1>[N:12]([C@@H:15]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@H:16]([OH:19])[CH2:17][O:18][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])=[N+:13]=[N-:14]

Participants

6

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 11117244(2S,3S)-3-azido-4-phenylbutane-1,2-diol

Product 1

HCID 117602043(S)-azido-4-phenyl-1-(p-toluenesulphonyloxy)-2(S)-butanolYield 82.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

1.05 g (5.5 mmol) of p-toluenesulphonyl chloride were added to a solution of 0.95 g (4.6 mmol) of 3(S)-azido-4-phenyl-1,2(S)-butanediol and 30 mg of 4-dimethylaminopyridine in a mixture of 30 ml of dichloromethane and 5 ml of pyridine. The resulting solution was stirred at room temperature for 48 hours. The solvents were removed under reduced pressure and the oily residue was partitioned between water and ethyl acetate. The aqueous phase was back-extracted twice with ethyl acetate. The organic phases were combined, washed with 10% aqueous sulphuric acid and with sodium chloride solution, dried over anhydrous magnesium sulphate and evaporated to dryness. Purification of the crude product by flash chromatography on silica gel using n-hexane/ethyl acetate (3:1) for the elution gave 1.37 g of 3(S)-azido-4-phenyl-1-(p-toluenesulphonyloxy)-2(S)-butanol in the form of a viscous oil: MS: m/e 362 [M+H]+.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe oily residue was partitioned between water and ethyl acetate
  3. extractionThe aqueous phase was back-extracted twice with ethyl acetate
  4. washwashed with 10% aqueous sulphuric acid and with sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated to dryness
  7. customPurification of the crude product by flash chromatography on silica gel
  8. washfor the elution

Sources & evidence

ORD record
ord-906798da84414b789ff88dd66f2471b5
Source dataset
uspto-grants-1996_05
Patent number
US05516913

Reaction notes

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