4-Toluenesulfonyl chloride → (3aRS,4RS,6SR,7aSR)-6-p-toluenesulphonyloxymethyl-4-(2-fluorophenyl)-2-[2-(1-pyrrolidinyl)phenylacetyl]perhydroisoindol-4-ol

HRID 1599153Notes

Reaction equation

HRID 1599153 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:11][CH:10]2[CH:6]([CH2:7][N:8]([C:12](=[O:25])[CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:9]2)[C:5]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])([OH:26])[CH2:4]1.[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1>C(N(CC)CC)C>[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40]([O:1][CH2:2][CH:3]2[CH2:11][CH:10]3[CH:6]([CH2:7][N:8]([C:12](=[O:25])[CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)[CH2:9]3)[C:5]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[F:33])([OH:26])[CH2:4]2)(=[O:42])=[O:41])=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 86752420(3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(2-fluorophenyl)-2-[2-(1-pyrrolidinyl)phenylacetyl]perhydroisoindol-4-ol

Product 1

HCID 86752419(3aRS,4RS,6SR,7aSR)-6-p-toluenesulphonyloxymethyl-4-(2-fluorophenyl)-2-[2-(1-pyrrolidinyl)phenylacetyl]perhydroisoindol-4-olYield 26.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The procedure is as described for Example 13, starting from 0.2 g of (3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(2-fluorophenyl)-2-[2-(1-pyrrolidinyl)phenylacetyl]perhydroisoindol-4-ol, 0.168 g of p-toluenesulphonyl chloride and 0.124 cm3 of triethylamine, and gives 0.07 g of (3aRS,4RS,6SR,7aSR)-6-p-toluenesulphonyloxymethyl-4-(2-fluorophenyl)-2-[2-(1-pyrrolidinyl)phenylacetyl]perhydroisoindol-4-ol in the form of a thick white foam.

Sources & evidence

ORD record
ord-eedb23fb2fc24cb0a6de5046c40982df
Source dataset
uspto-grants-1998_04
Patent number
US05739351

Reaction notes

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