反应 #157312

反应方程式

triethylamine

DMSO

oxalyl chloride

1-benzyl 4-tert-butyl 2-(hydroxymethyl)piperazine-1,4-dicarboxylate

→

1-benzyl 4-tert-butyl 2-formylpiperazine-1,4-dicarboxylate

溶剂

CH2Cl2

CH2Cl2

water

CH2Cl2

反应条件

后处理

1. 1
   workup.WAITAfter 15 min.
2. 2
   workup.WAITAfter 1 h
3. 3
   其他the organics were separated
4. 4
   萃取the aqueous layer was extracted with CH2Cl2 (3×100 mL)
5. 5
   洗涤The combined organics were washed with brine (3×150 mL), 1% HCl (3×150 mL), water (150 mL), and 5% NaHCO3 (3×150 mL)
6. 6
   干燥The organics were dried over Na2SO4
7. 7
   过滤filtered
8. 8
   浓缩concentrated under reduced pressure

实验过程

A solution of DMSO (1.41 mL, 19.9 mmol) in CH2Cl2 (5 mL) was added to a solution of oxalyl chloride (0.87 mL, 9.9 mmol) in CH2Cl2 (25 mL) at −60° C. After 5 min, a solution of 1-benzyl 4-tert-butyl 2-(hydroxymethyl)piperazine-1,4-dicarboxylate (3.16 g, 9.03 mmol) in CH2Cl2 (5 mL) was added. After 15 min., triethylamine (6.3 mL, 45 mmol) was added, and the reaction mixture was allowed to warm to rt. After 1 h, water (100 mL) was added, the organics were separated, and the aqueous layer was extracted with CH2Cl2 (3×100 mL). The combined organics were washed with brine (3×150 mL), 1% HCl (3×150 mL), water (150 mL), and 5% NaHCO3 (3×150 mL). The organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. This gave 3.07 g (98%) of the desired product as a thick oil. Rf=0.10 in 30% EtOAc/Hexane.

来源