1-Bromo-4-isopropylbenzene → methyl(3aRS,4SR,7RS,7aRS)-2-benzyl-7-(4-isopropylphenyl)-7-hydroxy-4-phenyloctahydroisoindole-3a-carboxylate

HRID 849603Notes

Reaction equation

HRID 849603 reaction equation
[CH3:1][O:2][C:3]([C:5]12[CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][C:10](=[O:20])[CH:9]1[CH2:8][N:7]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:6]2)=[O:4].[CH:28]([C:31]1[CH:36]=[CH:35][C:34]([Mg]Br)=[CH:33][CH:32]=1)([CH3:30])[CH3:29].BrC1C=CC(C(C)C)=CC=1.[Mg]>C(OCC)C>[CH3:1][O:2][C:3]([C:5]12[CH:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:12][CH2:11][C:10]([C:34]3[CH:35]=[CH:36][C:31]([CH:28]([CH3:30])[CH3:29])=[CH:32][CH:33]=3)([OH:20])[CH:9]1[CH2:8][N:7]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:6]2)=[O:4]

Participants

6

Reactant 4

HCID 114621-Bromo-4-isopropylbenzeneHCID 5462224MagnesiumHCID 11302988methyl(3aRS,4SR,7aRS)-2-benzyl-7-oxo-4-phenyloctahydroisoindole-3a-carboxylateHCID 178439193HCID 178439193, compound

Product 1

HCID 86755055methyl(3aRS,4SR,7RS,7aRS)-2-benzyl-7-(4-isopropylphenyl)-7-hydroxy-4-phenyloctahydroisoindole-3a-carboxylateYield 41%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

By carrying out the reaction as in Stage A of Example 1, but from 6 g of methyl(3aRS,4SR,7aRS)-2-benzyl-7-oxo-4-phenyloctahydroisoindole-3a-carboxylate in 60 cm3 of dry diethyl ether and from a solution of 4-isopropylphenylmagnesium bromide, prepared at the time of use from 4 g of 4-bromoisopropylbenzene and 0.52 g of magnesium turnings in 7 cm3 of dry diethyl ether, for eighteen hours at room temperature, 3.3 g (41%) of methyl(3aRS,4SR,7RS,7aRS)-2-benzyl-7-(4-isopropylphenyl)-7-hydroxy-4-phenyloctahydroisoindole-3a-carboxylate were obtained, after purification by flash chromatography on silica gel (230-400 mesh), elution being carried out with a gradient of mixtures of cyclohexane and of ethyl acetate (from 98/2 to 80/20 by volume), in the form of a yellow oil, the characteristic of which was as follows:

Workup

  1. customthe reaction as in Stage A of Example 1

Sources & evidence

ORD record
ord-25611443ebc8499e9175309a85a19121
Source dataset
uspto-grants-2000_01
Patent number
US06013662

Reaction notes

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