4-Toluenesulfonyl chloride → (3aRS,4RS,6SR,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-6-tosylmethylperhydroisoindol-4-ol

HRID 1599157Notes

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.O[CH2:13][CH:14]1[CH2:22][CH:21]2[CH:17]([CH2:18][N:19]([C:23](=[O:33])[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31][CH3:32])[CH2:20]2)[C:16]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[O:41][CH3:42])([OH:34])[CH2:15]1.C(N(CC)CC)C>ClCCl>[CH3:42][O:41][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[C:16]1([OH:34])[CH2:15][CH:14]([CH2:13][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:22][CH:21]2[CH:17]1[CH2:18][N:19]([C:23](=[O:33])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH3:32])[CH2:20]2

Participants

Conditions

Temperature: 20 °C

Procedure

3.05 g of p-toluenesulphonyl chloride are added to a solution of 3.4 g of (3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol and 2.24 cm3 of triethylamine in 150 cm3 of dichloromethane. The mixture is stirred at 20° C. for 20 hours, washed with 100 cm3 of water, dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). 4.1 g of (3aRS,4RS,6SR,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-6-tosylmethylperhydroisoindol-4-ol are obtained in the form of a thick white foam.

Workup

washwashed with 100 cm3 of water
dry with materialdried over magnesium sulphate
concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record: ord-8e65d24bb8884f54b8d9ac6ab7909de5
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739351

Reaction notes

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