Tetrabutylammonium Fluoride → 7-Methoxy-3,3-dimethyl-2-(3,4,5-trimethoxy-benzyl)-1,2,3,4-tetrahydro-isoquinolin-6-ol
Reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH3:19][O:20][C:21]1[CH:30]=[C:29]2[C:24]([CH2:25][C:26]([CH3:45])([CH3:44])[N:27]([CH2:31][C:32]3[CH:37]=[C:36]([O:38][CH3:39])[C:35]([O:40][CH3:41])=[C:34]([O:42][CH3:43])[CH:33]=3)[CH2:28]2)=[CH:23][C:22]=1[O:46][Si](C(C)C)(C(C)C)C(C)C.COC1C=C(C=CC=1)CN1C(C)(C)CC2C(=CC(OC)=C(O)C=2)C1>>[CH3:19][O:20][C:21]1[CH:30]=[C:29]2[C:24]([CH2:25][C:26]([CH3:44])([CH3:45])[N:27]([CH2:31][C:32]3[CH:33]=[C:34]([O:42][CH3:43])[C:35]([O:40][CH3:41])=[C:36]([O:38][CH3:39])[CH:37]=3)[CH2:28]2)=[CH:23][C:22]=1[OH:46]Participants
Reactant 3
Product 1
Procedure
TBAF deprotection of 227 (in analogy to the synthesis of 228) afforded the title compound (95 mg, 71%) as a yellow oil that crystallised on trituration with DCM/hexane to afford a yellow powder. mp=143-147° C. 1H NMR (270 MHz; CDCl3) 1.17 (6H, s, 2×CH3), 2.66 (2H, s, CH2), 3.52 (2H, s, CH2), 3.60 (2H, s, CH2), 3.82 (3H, s, OCH3), 3.83 (6H, s, 2×OCH3), 3.84 (3H, s, OCH3), 5.44 (1H, brs, OH), 6.50 (1H, s, CH), 6.53 (1H, s, CH), 6.60 (2H, s, 2×CH). 13C NMR (100 MHz; CDCl3) 23.82 (CH3), 42.41 (CH2), 50.02 (CH2), 52.53 (C), 53.78 (CH2), 55.88 (OCH3), 56.05 (OCH3), 60.84 (OCH3), 105.02 (CH), 110.68 (CH), 111.73 (CH), 125.62 (C), 126.85 (C), 136.44 (C), 143.54 (C), 145.02 (C), 153.08 (C). LC/MS (ES−) tr=1.17 min, m/z 386.26 (M−H)−. HRMS (ES+) calcd. for C22H30NO5 (M++H) 388.2118, found 388.2111. HPLC tr=2.73 min (>82%).
Sources & evidence
- ORD record
- ord-ac8cbbdad0094b969b9e16da3f2c17cc
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394825B2
Reaction notes
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