Reacción #214352

ord-d50eea50dbfe487d9bfa10340f28cf0f

Ecuación de reacción

CC(=O)OCC(=O)[C@@]1(OC(C)=O)CC[C@H]2[C@@H]3CC=C4C=C(OC(C)=O)CC[C@]4(C)[C@@]34O[C@H]4C[C@@]21C
9β,11β-epoxy-3,17,21-triacetoxy-pregna 3,5-diene-20-one
→
CC(=O)OCC(=O)[C@@]1(OC(C)=O)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)CC[C@]4(C)[C@@]34O[C@H]4C[C@@]21C
9β,11β-epoxy-6α-fluoro-17α,21-diacetoxy-4-pregnen-3,20-dione
Rendimiento 96.2%

Reactantes

CC(=O)OCC(=O)[C@@]1(OC(C)=O)CC[C@H]2[C@@H]3CC=C4C=C(OC(C)=O)CC[C@]4(C)[C@@]34O[C@H]4C[C@@]21C
9β,11β-epoxy-3,17,21-triacetoxy-pregna 3,5-diene-20-one
—
perchlorylfluoride

Reactivos

Ninguno

Disolventes

C1COCCO1
dioxane
O
water
c1ccncc1
pyridine

Condiciones de reacción

Temperatura
-10°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

17,5 g of 9β,11β-epoxy-3,17,21-triacetoxy-pregna 3,5-diene-20-one, prepared as described in Example I were dissolved in a mixture of 200 ml dioxane, 90 ml water, 10 ml pyridine, with the temperature being maintained at -10° C. Next a total quantity of approximately 4 g perchlorylfluoride was introduced at this temperature over a period of 4 hours. The further procedure was as described in Example IX; 16 g 9β,11β-epoxy-6α-fluoro-17α,21-diacetoxy-4-pregnen-3,20-dione were obtained.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04255331uspto-grants-1981_03