Water → 1'-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,5-triazin-2-yl]-1,4'-bipiperidinyl-3-ol

HRID 2175088ノート

反応式

HRID 2175088 の反応式
C(=O)([O-])[O-].[Na+].[Na+].Cl[C:8]1[N:13]=[CH:12][N:11]=[C:10]([N:14]2[CH2:19][CH2:18][CH:17]([N:20]3[CH2:25][CH2:24][CH2:23][CH:22]([OH:26])[CH2:21]3)[CH2:16][CH2:15]2)[N:9]=1.CC1(C)C(C)(C)OB([C:35]2[CH:44]=[CH:43][C:42]3[C:41]([CH3:46])([CH3:45])[CH2:40][CH2:39][C:38]([CH3:48])([CH3:47])[C:37]=3[CH:36]=2)O1.O>C1(C)C=CC=CC=1.C(O)C.O>[CH3:45][C:41]1([CH3:46])[CH2:40][CH2:39][C:38]([CH3:48])([CH3:47])[C:37]2[CH:36]=[C:35]([C:8]3[N:13]=[CH:12][N:11]=[C:10]([N:14]4[CH2:19][CH2:18][CH:17]([N:20]5[CH2:25][CH2:24][CH2:23][CH:22]([OH:26])[CH2:21]5)[CH2:16][CH2:15]4)[N:9]=3)[CH:44]=[CH:43][C:42]1=2

参加物

6

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 112439294,4,5,5-Tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolaneHCID 532524851-[1-(4-Chloro-1,3,5-triazin-2-yl)piperidin-4-yl]piperidin-3-ol

生成物 1

HCID 532504051'-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,5-triazin-2-yl]-1,4'-bipiperidinyl-3-ol

試薬・触媒・溶媒 1

HCID 86587398Ethanol toluene water溶媒

反応条件

温度
90 °C

実験手順

45 mg (0.42 mmol) of sodium carbonate are added to 50 mg (0.17 mmol) of 1′-(4-chloro-1,3,5-triazin-2-yl)-1,4′-bipiperidinyl-3-ol and 139 mg (0.42 mmol) of 4,4,5,5-tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane in 3.2 ml of toluene/ethanol/water (3.2/3.2/1). The reaction mixture is degassed a number of times, and 19 mg (0.017 mmol) of tetrakis-(triphenylphosphine)palladium(0) are added under nitrogen atmosphere, the mixture is treated in an ultrasound bath for 10 min and subsequently heated at 90° C. for 5 h. Water is added to the reaction mixture, which is then extracted three times with ethyl acetate/ether. The combined organic phases are dried over Na2SO4 and evaporated. The crude product is purified by means of preparative HPLC.

後処理

  1. additionare added under nitrogen atmosphere
  2. additionthe mixture is treated in an ultrasound bath for 10 min
  3. extractionis then extracted three times with ethyl acetate/ether
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. customevaporated
  6. customThe crude product is purified by means of preparative HPLC

出典と根拠

ORDレコード
ord-13578d4c243e4abc8f1e0d5c41f7dbd9
出典データセット
uspto-grants-2015_06
特許番号
US09062015B2

反応ノート

読み込み中…