反应 #1900

反应方程式

trans-7-chloro-5-(2-chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid

N-methylmorpholine

sodium borohydride

ethyl chlorocarbonate

→

trans-7-chloro-5-(2-chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-ethanol

收率 99.8%

溶剂

tetrahydrofuran

methanol

反应条件

后处理

1. 1
   workup.ADDITIONwas added dropwise to the solution
2. 2
   workup.STIRRINGThe mixture was stirred for one hour at room temperature
3. 3
   浓缩concentrated
4. 4
   workup.ADDITIONAfter the addition of 200 ml of 1N hydrochloric acid
5. 5
   萃取the concentrate was extracted with 200 ml of ethyl acetate
6. 6
   洗涤The organic layer was washed with a saturated sodium bicarbonate aqueous solution
7. 7
   干燥dried over anhydrous magnesium sulfate
8. 8
   其他The solvent was evaporated off under reduced pressure
9. 9
   其他The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=1:1)

实验过程

In 200 ml of tetrahydrofuran was dissolved 14.7 g of trans-7-chloro-5-(2-chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid obtained in Example 2 and 4.51 ml of N-methylmorpholine. To the solution was added 3.92 ml of ethyl chlorocarbonate at -10° C.; the mixture was then stirred for 15 minutes. After the addition of 3.86 g of sodium borohydride, 200 ml of methanol was added dropwise to the solution. The mixture was stirred for one hour at room temperature and then concentrated. After the addition of 200 ml of 1N hydrochloric acid, the concentrate was extracted with 200 ml of ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate aqueous solution and dried over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=1:1) to yield 14.2 g of trans-7-chloro-5-(2-chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-ethanol as colorless crystals, m.p. 157° to 159° C.

来源