Reaktion #70406

ord-e24ff23a939d43e0b0c3f559f688a598

Reaktionsgleichung

C[C@]12CC[C@H](O)CC1C(=O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-hydroxyandrostane-6,17-dione
CC(C)(C)OC(=O)N1CC(C(=O)O)C1
1-(tert-butoxycarbonyl)-3-azetidinecarboxylic acid
→
CC(C)(C)OC(=O)N1CC(C(=O)O[C@H]2CC[C@@]3(C)C(C2)C(=O)C[C@@H]2[C@@H]3CC[C@]3(C)C(=O)CC[C@@H]23)C1
3β-(N-(tert-Butoxycarbonyl)azetidin-3-ylcarbonyloxy)androstane-6,17-dione
Ausbeute 65.0%

Edukte

C[C@]12CC[C@H](O)CC1C(=O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-hydroxyandrostane-6,17-dione
CC(C)(C)OC(=O)N1CC(C(=O)O)C1
1-(tert-butoxycarbonyl)-3-azetidinecarboxylic acid

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Prepared in 65% yield from 3β-hydroxyandrostane-6,17-dione and 1-(tert-butoxycarbonyl)-3-azetidinecarboxylic acid by the procedure described in Prepn. 43. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.66 (1H, m), 4.50-1.00 (29H, m), 1.35 (9H, s), 0.78 (3H, s), 0.69 (3H, s).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08536160B2uspto-grants-2013_09