تفاعل #948820

ord-990edd6dac1548d3a5c5d4640812abd9

معادلة التفاعل

C[C@]12CC[C@H](OCc3ccccc3)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β,16α-dihydroxyandrost-5-en-17-one 3β-acetate
C[C@]12CC[C@H](OCc3ccccc3)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-benzyloxy-5-androsten-17-one
CCN(CC)C(F)(F)C(F)Cl
diethyl (2-chloro-1,1,2-trifluoroethyl)amine
→
C=C[C@H]1C=C2C[C@@H](O)CC[C@]2(C)[C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@H]12
16α-fluoro-3β-hydroxyandrost-5-en-17-one 3-acetate
C=C[C@H]1C=C2C[C@@H](O)CC[C@]2(C)[C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@H]12
3β-hydroxy-7β-ethenyl-5-androsten-17-one

المتفاعلات

C[C@]12CC[C@H](OCc3ccccc3)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β,16α-dihydroxyandrost-5-en-17-one 3β-acetate
C[C@]12CC[C@H](OCc3ccccc3)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-benzyloxy-5-androsten-17-one
CCN(CC)C(F)(F)C(F)Cl
diethyl (2-chloro-1,1,2-trifluoroethyl)amine

الكواشف

لا شيء

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

الإجراء التجريبي

Reaction of 3β,16α-dihydroxyandrost-5-en-17-one 3β-acetate 1 with a fluorinating agent such as diethyl (2-chloro-1,1,2-trifluoroethyl)amine affords 16α-fluoro-3β-hydroxyandrost-5-en-17-one 3-acetate 3. Hydrolysis of the ester with aqueous acid yields 16α-fluoro-3β-hydroxyandrost-5-en-17-one, 2a. ##STR47##

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05714481uspto-grants-1998_02