Methanol → Toluene-4-sulfonic acid 4-(6-hydroxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl ester

HRID 397040Notes

Reaction equation

B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]([C:17]1[CH:22]=[CH:21][C:20]([O:23][S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])=[CH:19][CH:18]=1)[N:12]([C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])[CH2:11][CH2:10]2.CO>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]([C:17]1[CH:18]=[CH:19][C:20]([O:23][S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])=[CH:21][CH:22]=1)[N:12]([C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])[CH2:11][CH2:10]2

Participants

Conditions

Temperature: 0 °C

Procedure

A 1M solution of BBr3 in CH2Cl2 (16.2 ml, 16.2 mmol) was added slowly to a solution of toluene-4-sulfonic acid 4-(6-methoxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl ester (7.459 g, 14.8 mmol) in anhydrous CH2Cl2 (500 ml) at 0° C. under N2. After stirring at 0° C. for 1 hr, the reaction mixture was warmed to rt and stirred at rt for 18 hr. MeOH (250 ml) was slowly added with stirring and the resulting solution was concentrated in vacuo to give 9.793 g of brown residue. Purification by flash chromatography, eluting with hexane:EtOAc (7:3) gave 2.764 g (38% yield) of white solid.

Workup

temperaturethe reaction mixture was warmed to rt
stirringstirred at rt for 18 hr
stirringwith stirring
concentrationthe resulting solution was concentrated in vacuo

Sources & evidence

ORD record: ord-93b12d8eed2842e3b4bc59137fddba72
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608203B2

Reaction notes

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