Reaction #1747893

ord-055bcad9300748e394249e541090ddc7

Reaction equation

C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2O
estradiol
O=C(O)c1ccc([N+](=O)[O-])cc1
p-nitrobenzoic acid
→
C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2O.O=C([O-])c1ccc([N+](=O)[O-])cc1
p-nitrobenzoate estradiol

Reactants

C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2O
estradiol
O=C(O)c1ccc([N+](=O)[O-])cc1
p-nitrobenzoic acid
—
3-O-benzyl-17

Reagents

None

Solvents

Cc1ccccc1
toluene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Inversion of the configuration of the 17-position of oestradiol was achieved using a Misunobu reaction. The complex formed by triphenylphosphine and DEAD was reacted with the 3-O-benzyl-17-□-estradiol BLE99051 and p-nitrobenzoic acid at 80° C. in toluene to give the 3-O-benzyl-17-□-p-nitrobenzoate-estradiol BLE99053. Hydrolysis of the ester moiety of BLE99053 using potassium carbonate afforded cleanly the 3-O-benzyl-17-□-estradiol BLE99056 in a 84.5% yield.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08030296B2uspto-grants-2011_10