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Hydrochloric Acid → HCID 18401805、化合物

HRID 377285
ノート
印刷プレビュー

反応式

HRID 377285 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([CH3:11])[N:6]([C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:5]2.C([Li])CCC.C([O:39][B:40](OC(C)C)[O:41]C(C)C)(C)C.Cl>O1CCCC1.CCCCCC>[CH3:11][CH:7]1[C:8]2[C:4](=[CH:3][C:2]([B:40]([OH:41])[OH:39])=[CH:10][CH:9]=2)[CH2:5][N:6]1[C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 18629350HCID 18629350、化合物HCID 178418339Butyllithium

生成物 1

HCID 18401805HCID 18401805、化合物収率 80.9%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒
HCID 8058
Hexane
溶媒

反応条件

温度
-72 °C

実験手順

In 75 ml of anhydrous tetrahydrofuran was dissolved 15.0 g of (+)-5-bromo-1-methyl-2-trityliso-indoline, and the solution was cooled to -72° C. under a nitrogen atmosphere, after which 22.3 ml of a 1.63 M solution of n-butyllithium in n-hexane was added dropwise thereto over a period of 15 minutes, and the resulting mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added dropwise 7.45 g of triisopropoxyborane at -72° C. over a period of 20 minutes, and the resulting mixtuere was stirred at the same temperature for 30 minutes. The reaction mixture was added to 75 ml of ice water and the pH was adjusted to 6.8 with lN hydrochloric acid, after which the organic layer was separated. The organic layer obtained was washed with water, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. Cyclohexane was added to the resulting residue and the crystals were collected by filtration to obtain 11.2 g ofcolorless (+)-1-methyl-2-tritylisoindoline-5-boronic acid.

後処理

  1. stirringthe resulting mixtuere was stirred at the same temperature for 30 minutes
  2. customafter which the organic layer was separated
  3. customThe organic layer obtained
  4. washwas washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. additionCyclohexane was added to the resulting residue
  9. filtrationthe crystals were collected by filtration

出典と根拠

ORDレコード
ord-a66decf5b1d54b8381f43082dad26a21
出典データセット
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06025370

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート