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

HRID 1696841노트

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HRID 1696841 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 84.1%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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).

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 Biotage silica gel column chromatography
  7. washeluting with a mixture of ethyl acetate (0-3%) in dichloromethane

출처 및 근거

ORD 기록
ord-e69cbf8852574f689d3716e2e4810291
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163758B2

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