تفاعل #1900

معادلة التفاعل

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

المردود 99.8%

المذيبات

tetrahydrofuran

methanol

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر