4-Toluenesulfonyl chloride → (3aRS,6SR,7aSR)-2-tert-butyloxycarbonyl-6-tosyloxymethylperhydroisoindol-4-one

HRID 1599135Notes

Reaction equation

HRID 1599135 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][CH2:13][CH:14]1[CH2:22][CH:21]2[CH:17]([CH2:18][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:20]2)[C:16](=[O:30])[CH2:15]1.C(N(CC)CC)C>ClCCl>[C:26]([O:25][C:23]([N:19]1[CH2:18][CH:17]2[CH:21]([CH2:22][CH:14]([CH2:13][O:12][S:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=3)(=[O:9])=[O:8])[CH2:15][C:16]2=[O:30])[CH2:20]1)=[O:24])([CH3:27])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 18931561(3aRS,6SR,7aSR)-6-hydroxymethyl-2-tert-butyloxycarbonylperhydroisoindol-4-one

Product 1

HCID 18931565(3aRS,6SR,7aSR)-2-tert-butyloxycarbonyl-6-tosyloxymethylperhydroisoindol-4-oneYield 64.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

17.5 g of p-toluenesulphonyl chloride are added to a solution of 12.4 g of (3aRS,6SR,7aSR)-6-hydroxymethyl-2-tert-butyloxycarbonylperhydroisoindol-4-one and 12.9 cm3 of triethylamine in 250 cm3 of dichloromethane. The mixture is stirred at room temperature for 20 hours, washed with 200 cm3 of water, dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is chromatographed on a silica gel column (diameter 7 cm, particle size 0.06-0.20 mm, height 70 cm), eluting under a pressure of 0.7 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (60:40 by volume) and collecting fractions of 250 cm3. Evaporation to dryness of fractions 16 to 24 under reduced pressure (2.7 kPa) gives 12.6 g of (3aRS,6SR, 7aSR)-2- tert-butyloxycarbonyl-6-tosyloxymethylperhydroisoindol-4-one in the form of an oil.

Workup

  1. washwashed with 200 cm3 of water
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe residue obtained
  5. customis chromatographed on a silica gel column (diameter 7 cm, particle size 0.06-0.20 mm, height 70 cm)
  6. washeluting under a pressure of 0.7 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (60:40 by volume)
  7. customcollecting fractions of 250 cm3
  8. customEvaporation to dryness of fractions 16 to 24 under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-4d411a71274041e7a7200198df7d7b58
Source dataset
uspto-grants-1998_04
Patent number
US05739351

Reaction notes

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