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

HRID 1696856ノート

反応式

HRID 1696856 の反応式
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

参加物

6

反応物 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 86607679N-Benzyl-N-[2-benzyloxy-5-(2-bromoacetyl)phenyl]methanesulfonamide

生成物 1

HCID 66860109N-Benzyl-N-[2-benzyloxy-5-(2-bromo-1-(R)-hydroxyethyl)phenyl]methane-sulfonamide収率 95%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of BH3.THF in THF (1 M, 30.70 mmol) was added to a mixture of N-benzyl-N-[2-benzyloxy-5-(2-bromoacetyl)phenyl]methanesulfonamide (131) (25.00 g, 51.20 mmol) and R-methyl-CBS-oxazoborolidine (1 M in toluene, 5.10 mL, 5.10 mmol) in anhydrous THF (150 mL). The reaction mixture was stirred at 0° C. for 15 min and then at rt for 16 h. Methanol (100 mL) was then slowly added to quench the reaction. After removal of solvent by rotary evaporation, the resulting residue was purified by column chromatography (silica gel, dichloromethane only) to give desired bromo alcohol 132 as an orange oil (23.80 g, 95% yield): 1H NMR (500 MHz, CDCl3) δ 2.86 (s, 3H), 3.30-3.38 (m, 2H), 4.70 (m, 3H), 5.11 (s, 2H), 7.00 (m, 2H), 7.21 (m, 5H), 7.28 (d, 1H), 7.42 (m, 5H).

後処理

  1. waitat rt for 16 h
  2. customto quench
  3. customthe reaction
  4. customAfter removal of solvent
  5. customby rotary evaporation
  6. customthe resulting residue was purified by column chromatography (silica gel, dichloromethane only)

出典と根拠

ORDレコード
ord-614bb9b63ebf4d598a89ecd4af948dec
出典データセット
uspto-grants-2012_04
特許番号
US08163758B2

反応ノート

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