Methanol → 5-((1R)-2-bromo-1-hydroxyethyl)-8-phenylmethoxy-1H-quinolin-2-one

HRID 14447

반응식

HRID 14447 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:20](=[O:23])[CH2:21][Br:22])=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.B.CO>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([OH:23])[CH2:21][Br:22])=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 6331BoraneHCID 8028TetrahydrofuranHCID 116678678-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline

생성물 1

HCID 115308845-((1R)-2-bromo-1-hydroxyethyl)-8-phenylmethoxy-1H-quinolin-2-one수율 81%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
-10 °C

실험 절차

8-Benzyloxy 5-(2-bromoacetyl)-1H-quinolin-2-one (90.0 g, 243 mmol) was placed under nitrogen and tetrahydrofuran (900 mL) was added followed by the catalyst described above (1.8 M in toluene, 15 mL, 27 mmol). The suspension was cooled to −10±5° C. in an ice/isopropanol bath. Borane (1.0 M in THF, 294 mL, 294 mmol) was added over 4 h. The reaction was then stirred an additional 45 min at −10° C. and then methanol (250 mL) was added slowly. The mixture was concentrated under vacuum and the residue was dissolved in boiling acetonitrile (1.3 L), filtered while hot and then cooled to room temperature. The crystals were filtered, washed with acetonitrile and dried under vacuum to give the title compound (72.5 g, 196 mmol, 81% yield, 95% ee, 95% pure by HPLC).

후처리

  1. concentrationThe mixture was concentrated under vacuum
  2. dissolutionthe residue was dissolved
  3. filtrationfiltered while hot and
  4. temperaturethen cooled to room temperature
  5. filtrationThe crystals were filtered
  6. washwashed with acetonitrile
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-c58d716fe38c465fa2ff04bb6e2aa689
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732441B2

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