4-tert-Butylphenylboronic acid → 7-(4-tert-Butylphenoxy)-isoquinoline-3-carboxylic acid

HRID 1984828Notes

Reaction equation

HRID 1984828 reaction equation
COC([C@@H]1CC2C(=CC(O)=CC=2)CN1C(OC(C)(C)C)=O)=O.C(C1C=CC(B(O)O)=CC=1)(C)(C)C.C[O:37][C:38]([C@@H:40]1[CH2:49][C:48]2[C:43](=[CH:44][C:45]([O:50][C:51]3[CH:56]=[CH:55][C:54]([C:57]([CH3:60])([CH3:59])[CH3:58])=[CH:53][CH:52]=3)=[CH:46][CH:47]=2)[CH2:42][N:41]1C(OC(C)(C)C)=O)=[O:39]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:57]([C:54]1[CH:55]=[CH:56][C:51]([O:50][C:45]2[CH:44]=[C:43]3[C:48]([CH:49]=[C:40]([C:38]([OH:39])=[O:37])[N:41]=[CH:42]3)=[CH:47][CH:46]=2)=[CH:52][CH:53]=1)([CH3:60])([CH3:58])[CH3:59]

Participants

5

Reactant 3

HCID 27343204-tert-Butylphenylboronic acidHCID 213113062-tert-butyl 3-methyl (3S)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-2,3-dicarboxylateHCID 68869404(3S)-7-(4-tert-butylphenoxy)-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester

Product 1

HCID 184576667-(4-tert-Butylphenoxy)-isoquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

The above phenol (1.20 g, 3.91 mmol) was reacted with 4-(tert-butyl)phenylboronic acid (1.6 eq., 6.26 mmol, 1.11 g ), copper(II) acetate (1.0 eq. 3.91 mmol, 710 mg) as desribed in general procedure G. Flash column chromatography on silica (ethyl acetate/hexanes) provided 750 mg of the desired product, (3S)-7-(4-tert-butylphenoxy)-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester.

Sources & evidence

ORD record
ord-17d470ec93c3465cb6391bc7127f2980
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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