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

HRID 14447

反応式

HRID 14447 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
-10 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c58d716fe38c465fa2ff04bb6e2aa689
出典データセット
uspto-grants-2010_06
特許番号
US07732441B2

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