Toluene → t-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-1H-pyrrol-1-yl)ethyl)-2-phenyl-1,3,2-dioxaborinan-4-yl)acetate

HRID 1925640ノート

反応式

HRID 1925640 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][C:11](=O)[CH:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[NH2:30][CH2:31][CH2:32][C@H:33]1[O:38][B:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:36][C@@H:35]([CH2:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:34]1.C(O)(=O)C(C)(C)C>C(N(CC)CC)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:30]([CH2:31][CH2:32][C@H:33]3[O:38][B:37]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[O:36][C@@H:35]([CH2:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:34]3)[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][C:9]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 1140TolueneHCID 6417Pivalic acidHCID 11449985t-butyl 2-((4R,6R)-6-(2-aminoethyl)-2-phenyl-1,3,2-dioxaborinan-4-yl)acetateHCID 147571731-(4-Fluorophenyl)-5-methyl-2-phenylhexane-1,4-dione

生成物 1

HCID 58112769t-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-1H-pyrrol-1-yl)ethyl)-2-phenyl-1,3,2-dioxaborinan-4-yl)acetate収率 79%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

反応条件

温度
22.5 °C

実験手順

To a nitrogen-filled flask, 126 g of 1-(4-fluorophenyl)-5-methyl-2-phenyl-1,4-hexanedione, 2.5 L of toluene, 41 ml of triethylamine, 160 g of t-butyl 2-((4R,6R)-6-(2-aminoethyl)-2-phenyl-1,3,2-dioxaborinan-4-yl)acetate and 33 ml of pivalic acid were added. The mixture was heated to reflux with stirring for 14 hours while removing water with a Dean-Stark trap. The reaction mixture was cooled slowly to 20-25° C. and washed with purified water, and the organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure, thus obtaining 194 g of the title compound as yellow oil.

後処理

  1. additionTo a nitrogen-filled flask
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. customwhile removing water with a Dean-Stark trap
  5. washwashed with purified water
  6. customthe organic layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-3749f65dcc8249c2a36b9a5ef9cb809a
出典データセット
uspto-grants-2012_05
特許番号
US08178697B2

反応ノート

読み込み中…