无水磷酸二氢钾 → CBZ-脯氨醇

HRID 21760

反应方程式

HRID 21760 反应方程式
[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13](O)=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].P([O-])([O-])([O-])=O.CCOCC>C1COCC1>[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[CH2:13][OH:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

参与物

5

反应物 3

HCID 1061无水磷酸二氢钾HCID 3283乙醚HCID 101987N-苄氧羰基-L-脯氨酸

产物 1

HCID 11096562CBZ-脯氨醇收率 113.6%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂2 次

反应条件

温度
0 °C

实验过程

To Carbobenzyloxy-L-proline (Aldrich, 9.80 g, 39.3 mmol) in THF (100 mL) at 0° C. was added BH3 -THF complex (Aldrich, 1M in THF, 100 mL, 100 mmol). The mixture was stirred at 0° C. for 2 hours, then at ambient temperature for 16 hr. The reaction mixture was poured into pH 7 phosphate buffer solution (500 mL) and ether (600 mL) and mixed well. The layers were separated and the aqueous portion was extracted with ether (500 mL). The combined organic layers were washed with brine (500 mL), dried (Na2SO4) and filtered. The solvents were evaporated in vacuo leaving the crude carbobenzyloxy-L-prolinol as an oil (10.5 g).

后处理

  1. waitat ambient temperature for 16 hr
  2. additionmixed well
  3. customThe layers were separated
  4. extractionthe aqueous portion was extracted with ether (500 mL)
  5. washThe combined organic layers were washed with brine (500 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customThe solvents were evaporated in vacuo

来源与证据

ORD记录
ord-8f1e1fc265ee4e8686e00515ef1a9f73
来源数据集
uspto-grants-1995_06
专利号
US05424444

关联笔记

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