Methanol → N-Benzyl-N-[2-benzyloxy-5-(2-bromo-1-(R)-hydroxyethyl)phenyl]methane-sulfonamide

HRID 1696841Notes

Reaction equation

B.C1COCC1.[CH2:7]([N:14]([C:19]1[CH:24]=[C:23]([C:25](=[O:28])[CH2:26][Br:27])[CH:22]=[CH:21][C:20]=1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[S:15]([CH3:18])(=[O:17])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CO>C1(C)C=CC=CC=1.C1COCC1>[CH2:7]([N:14]([C:19]1[CH:24]=[C:23]([C@@H:25]([OH:28])[CH2:26][Br:27])[CH:22]=[CH:21][C:20]=1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[S:15]([CH3:18])(=[O:17])=[O:16])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of BH3.THF in THF (1 M, 2.80 mL, 2.80 mmol) was added to a mixture of N-benzyl-N-[2-benzyloxy-5-(2-bromoacetyl)phenyl]methanesulfonamide (33) (1.09 g, 2.23 mmol) and R-methyl-CBS-oxazoborolidine (1 M in toluene, 0.45 mL, 0.45 mmol) in anhydrous THF (10 mL). The reaction mixture was stirred at 0° C. for 15 min and then at rt for 16 h. Methanol (5 mL) was slowly added to quench the reaction. After removal of solvent by rotary evaporation, the resulting residue was purified by Biotage silica gel column chromatography eluting with a mixture of ethyl acetate (0-3%) in dichloromethane to give the desired bromo alcohol 34 as a white solid (0.92 g, 84%): 1H NMR (500 MHz, CDCl3) δ 2.60 (s, 1H), 2.85 (s, 3H), 3.30 (m, 1H), 3.38 (m, 1H), 4.70 (m, 3H), 5.11 (s, 2H), 7.00 (m, 2H), 7.21 (m, 5H), 7.28 (d, 1H), 7.42 (m, 5H).

Workup

waitat rt for 16 h
customto quench
customthe reaction
customAfter removal of solvent
customby rotary evaporation
customthe resulting residue was purified by Biotage silica gel column chromatography
washeluting with a mixture of ethyl acetate (0-3%) in dichloromethane

Sources & evidence

ORD record: ord-e69cbf8852574f689d3716e2e4810291
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163758B2

Reaction notes

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