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Hydrochloric Acid → HCID 18401805, 화합물

HRID 377285
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HRID 377285 반응식
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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 18629350HCID 18629350, 화합물HCID 178418339Butyllithium

생성물 1

HCID 18401805HCID 18401805, 화합물수율 80.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매
HCID 8058
Hexane
용매

반응 조건

온도
-72 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a66decf5b1d54b8381f43082dad26a21
출처 데이터셋
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06025370

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