Ethyl Acetate → 4-((1R,2S)-2-(2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethylamino}-1-hydroxypropyl)phenol

HRID 30763Notes

Reaction equation

CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([B:15]2[O:19][C:18]([CH3:21])([CH3:20])[C:17]([CH3:23])([CH3:22])[O:16]2)=[CH:11][CH:10]=1)(=O)=O.[NH2:24][C@@H:25]([CH3:35])[C@@H:26]([C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)[OH:27].C(OCC)(=O)C>CN(C)C=O>[CH3:21][C:18]1([CH3:20])[C:17]([CH3:22])([CH3:23])[O:16][B:15]([C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][NH:24][C@@H:25]([CH3:35])[C@@H:26]([C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=3)[OH:27])=[CH:14][CH:13]=2)[O:19]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethyl methanesulfonate (1.20 g) and 4-((1R,2S)-2-amino-1-hydroxypropyl)phenol (1.76 g) in N,N-dimethylformamide (20 mL) was stirred at 80° C. for 5 hrs. Ethyl acetate was added to the reaction mixture. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:n-hexane/ethyl acetate=1/1, methylene chloride/methanol=9/1) to afford the title compound (0.24 g).

Workup

washThe organic layer was washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (eluent:n-hexane/ethyl acetate=1/1, methylene chloride/methanol=9/1)

Sources & evidence

ORD record: ord-8c7618feeee049eebb73358fc74bc42e
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423185B2

Reaction notes

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