(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮 → 8-苄氧基-5-（（R）-2-溴-1-羟乙基）-1H-喹啉酮

HRID 14447

反应方程式

HRID 14447 反应方程式
[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

参与物

6

反应物 4

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮HCID 6331BoraneHCID 8028四氢呋喃HCID 116678678-苄氧基-5-(2-溴乙酰基)-2-羟基喹啉

产物 1

HCID 115308848-苄氧基-5-（（R）-2-溴-1-羟乙基）-1H-喹啉酮收率 81%

试剂、催化剂与溶剂 1

HCID 1140甲苯溶剂

反应条件

温度
-10 °C

实验过程

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).

后处理

  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

来源与证据

ORD记录
ord-c58d716fe38c465fa2ff04bb6e2aa689
来源数据集
uspto-grants-2010_06
专利号
US07732441B2

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