Reacción #1876

Ecuación de reacción

trans-1-benzyl2-oxo-5-phenyl-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-propionic acid

sodium borohydride

lithium chloride

hydrochloric acid

→

trans-1-benzyl-3-(3-hydroxypropyl)-5-phenyl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one

Disolventes

tetrahydrofuran

ethanol

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGwas stirred for 2 hours at 60° C
2. 2
   LavadoThe ethyl acetate layer was washed with an aqueous solution of sodium hydrogencarbonate, which
3. 3
   Secadowas dried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
5. 5
   OtroThe residue was purified by means of a silica gel column chromatography (eluent, hexane:ethyl acetate=2:1)

Procedimiento

The mixture of 0.4 g of methyl ester of trans-1-benzyl2-oxo-5-phenyl-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-propionic acid obtained in Example 12, 0.16 g of sodium borohydride and 0.16 g of lithium chloride in 15 ml of tetrahydrofuran were stirred for 10 minutes at room temperature. To the resultant was added 30 ml of ethanol, which was stirred for 2 hours at 60° C. To the reaction mixture were added 100 ml of 1N hydrochloric acid and 150 ml of ethyl acetate. The ethyl acetate layer was washed with an aqueous solution of sodium hydrogencarbonate, which was dried over anhydrous magnesium sulfate, then the solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluent, hexane:ethyl acetate=2:1) to give 0.19 g of trans-1-benzyl-3-(3-hydroxypropyl)-5-phenyl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one as needles, m.p. 59°-62° C.

Fuente