四氧化硫 → Isoxazole, 3-methyl-5-[(2S)-1-methyl-2-pyrrolidinyl]- (9CI)

HRID 21767

反应方程式

HRID 21767 反应方程式
[BH4-].[Na+].[C:3]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=O)(OCC1C=CC=CC=1)=O.OS(O)(=O)=O>C1COCC1.CCOCC>[CH3:18][C:14]1[CH:15]=[C:15]([C@@H:14]2[CH2:18][CH2:19][CH2:20][N:13]2[CH3:3])[O:17][N:13]=1

参与物

6

反应物 3

HCID 1118四氧化硫HCID 101987N-苄氧羰基-L-脯氨酸HCID 4311764硼氢化钠

产物 1

HCID 119380Isoxazole, 3-methyl-5-[(2S)-1-methyl-2-pyrrolidinyl]- (9CI)收率 88%

试剂、催化剂与溶剂 2

HCID 3283乙醚溶剂2 次HCID 8028四氢呋喃溶剂

反应条件

温度
0 °C

实验过程

To a stirred suspension of sodium borohydride (7.59 g, 200 mmol) in 100 mL of THF cooled to 0° C. was added a solution of 20 g (80.28 mmol) of N-Cbz-L-proline, from step 24a above, in 50 mL of ether. To this solution was added dropwise a solution of 5 mL of H2SO4 in 20 mL of ether, with stirring and while maintaining the temperature below 20° C. The reaction mixture was warmed to room temperature and stirred for 16 hr. The reaction was quenched by the addition of 100 mL of methanol dropwise. The solvents were removed, 30 mL of 4N NaOH was added, and the mixture was extracted with ethyl acetate. The organic extract was dried over Na2SO4 and concentrated to afford the title product, 16.61 g (88 % yield).

后处理

  1. temperaturewhile maintaining the temperature below 20° C
  2. temperatureThe reaction mixture was warmed to room temperature
  3. stirringstirred for 16 hr
  4. customThe reaction was quenched by the addition of 100 mL of methanol dropwise
  5. customThe solvents were removed
  6. addition30 mL of 4N NaOH was added
  7. extractionthe mixture was extracted with ethyl acetate
  8. extractionThe organic extract
  9. dry with materialwas dried over Na2SO4
  10. concentrationconcentrated

来源与证据

ORD记录
ord-c9a6f38691244cecb730d2b45b58285c
来源数据集
uspto-grants-1995_06
专利号
US05424444

关联笔记

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