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

HRID 1696856노트

반응식

HRID 1696856 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-614bb9b63ebf4d598a89ecd4af948dec
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163758B2

반응 노트

불러오는 중…