Tetrabutylammonium Fluoride → tert-Butyl (4-(hydroxymethyl)-2-methoxyphenyl)carbamate
Reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[C:12]([O:24][CH3:25])[CH:11]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[C:12]([O:24][CH3:25])[CH:11]=1Participants
4
Procedure
To a solution of protected alcohol 7 (242.4 mg, 0.66 mmol) in THF (2.5 ml) was added a solution of 1M tetrabutylammonium fluoride in THF (0.73 ml, 0.73 mmol) and the mixture was stirred at room temperature for 24 hrs. The crude product was adsorbed on silica gel and purified by MPLC, eluting with hexanes/ethyl acetate 40%-50% gradient to give the title alcohol (92.9 mg, 56% yield). H-NMR (400 MHz, CD2Cl2): 8.85 (1H, brs) 7.78 (1H, d, J=8 Hz) 7.09 (1H, s) 6.82 (1H, dd, J=8 Hz, 0.4 Hz) 4.58 (2H, d, J=4 Hz) 3.5 (1H, t, J=4 Hz) 1.18 (9H, s).