3-Bromoanisole → methyl (3aRS,4SR,7RS,7aRS)-2-benzyl-7-hydroxy-7-(3-methoxyphenyl)-4-phenyloctahydroisoindole-3a-carboxylate

HRID 324657Notes

Reaction equation

HRID 324657 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[Mg].[Cl-].[Ce+3].[Cl-].[Cl-].[CH2:15]([N:22]1[CH2:30][C:29]2([C:31]([O:33][CH3:34])=[O:32])[CH:24]([C:25](=[O:41])[CH2:26][CH2:27][CH:28]2[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(OCC)C>[CH2:15]([N:22]1[CH2:30][C:29]2([C:31]([O:33][CH3:34])=[O:32])[CH:24]([C:25]([OH:41])([C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=3)[CH2:26][CH2:27][CH:28]2[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 169713-BromoanisoleHCID 24636Cerium(III) chlorideHCID 5462224MagnesiumHCID 11302988methyl(3aRS,4SR,7aRS)-2-benzyl-7-oxo-4-phenyloctahydroisoindole-3a-carboxylate

Product 1

HCID 86755047methyl (3aRS,4SR,7RS,7aRS)-2-benzyl-7-hydroxy-7-(3-methoxyphenyl)-4-phenyloctahydroisoindole-3a-carboxylateYield 48.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

By carrying out the reaction as in Stage A of Example 6, but from 1.56 cm3 (12.4 mmol) of 3-bromoanisole and from 302 mg (12.4 mmol) of magnesium turnings at reflux for one hour in 5 cm3 of dry diethyl ether, followed successively by 1.02 g (4.13 mmol) of anhydrous cerium chloride and by a solution of 1.5 g (4.13 mmol) of methyl (3aRS,4SR,7aRS)-2-benzyl-7-oxo-4-phenyloctahydroisoindole-3a-carboxylate, obtained in Stage B of Example 1, in 8 cm3 of diethyl ether, 945 mg (48%) of methyl (3aRS,4SR,7RS,7aRS)-2-benzyl-7-hydroxy-7-(3-methoxyphenyl)-4-phenyloctahydroisoindole-3a-carboxylate were obtained, after purification by flash chromatography on silica gel (230-400 mesh), elution being carried out with cyclohexane and then with a cyclohexane/ethyl acetate (80/20 by volume) mixture, in the form of a white solid, the characteristic of which was as follows:

Workup

  1. customthe reaction as in Stage A of Example 6

Sources & evidence

ORD record
ord-8e5ea5dbf63b47b48b456d423cb484e2
Source dataset
uspto-grants-2001_04
Patent number
US06218406B1

Reaction notes

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