Sodium t-butoxide → tert-Butyl (((1R,2R)-rel-2-(2-(cyclopropylmethoxy)-5-hydroxyphenyl)cyclopropyl)methyl)carbamate
Reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][CH2:8][C@@H:9]1[CH2:11][C@H:10]1[C:12]1[CH:17]=[C:16]([O:18]C(=O)C(C)(C)C)[CH:15]=[CH:14][C:13]=1[O:25][CH2:26][CH:27]1[CH2:29][CH2:28]1)([CH3:4])([CH3:3])[CH3:2].CC([O-])(C)C.[Na+]>CO>[C:1]([O:5][C:6](=[O:30])[NH:7][CH2:8][C@@H:9]1[CH2:11][C@H:10]1[C:12]1[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:13]=1[O:25][CH2:26][CH:27]1[CH2:29][CH2:28]1)([CH3:4])([CH3:2])[CH3:3]Participants
4
Procedure
A solution of compound 16 (127 mg, 0.304 mmol) in MeOH (1 mL) was treated with NaOtBu (146 mg, 1.52 mmol) at 0° C. After stirring at rt for 4 h, the reaction was quenched adding sat. NH4Cl (2 mL) and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography using gradient elution from 0% EtOAc-hexane to 30% EtOAc-hexane to afford the title compound as a thick oil (95 mg, 94% yield). 1H NMR (400 MHz, CDCl3) δ 6.68-6.60 (m, 2 H), 6.48-6.44 (m, 2 H), 5.48 (bs, 1H), 3.94-3.90 (m, 1 H), 3.70-3.65 (m, 2 H), 2.64-2.60 (m, 1 H), 1.84-1.81 (m, 1 H), 1.45-1.39 (m, 10 H), 0.98-0.95 (m, 2 H), 0.76-0.73 (m, 1 H), 6.64-6.62 (m, 2 H), 0.35-0.34 (m, 2 H).