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

HRID 1599135ノート

反応式

HRID 1599135 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4d411a71274041e7a7200198df7d7b58
出典データセット
uspto-grants-1998_04
特許番号
US05739351

反応ノート

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