Cl.C(OCC)C.C([Si](C)(C)[O:12][CH2:13][C@H:14]([NH-:25])[C:15]1[CH:16]=[N:17][C:18]([O:21][CH2:22][CH2:23][CH3:24])=[CH:19][CH:20]=1)(C)(C)C>CO>[NH2:25][C@H:14]([C:15]1[CH:16]=[N:17][C:18]([O:21][CH2:22][CH2:23][CH3:24])=[CH:19][CH:20]=1)[CH2:13][OH:12]A 2.00 M solution of hydrogen chloride in diethyl ether (28 mL, 56 mmol) was added to a stirred solution of [(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(6-propoxy-pyridin-3-yl)-ethyl]-amide (2.33 g, 5.62 mmol) dissolved in MeOH (11 mL) at 0° C. under Ar. After the addition was completed the cooling bath was removed and the solution was stirred at room temperature overnight. The mixture was then evaporated to dryness and the residue was suspended in methylene chloride and transferred to a short silica gel column. After eluding with EtOAc:EtOH:Et3N (90:5:5) (R)-2-Amino-2-(6-propoxy-pyridin-3-yl)-ethanol, IM36, was obtained as an oil (0.813 g, 74%). The overall yield from 5-bromo-2-propoxypyridine IM3 was 36%.
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