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11β-(trimethylsiloxy)-16α,17α,21-trimethylpregna-1,4-dien-3,20-dione
rimexolone
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 0 - 20℃; for 2.5h; Hydrolysis; | 97% |
prednisolon
rimexolone
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: pyridine / 5 °C 2.1: NaI / acetone / 20 °C 3.1: NaI; HOAc / acetone / Heating 4.1: 1.40 g / semicarbazide*HCl / H2O; acetic acid / 9.7 h / 80 - 85 °C 5.1: 1.42 g / DMAP; pyridine / 25 h 6.1: LiN(TMS)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.17 h / -65 - -60 °C 6.2: 82 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.03 h / -65 - 10 °C 7.1: 85.5 percent / CuCN / various solvent(s); tetrahydrofuran / 0.22 h / -45 °C 8.1: 63 percent / 4A molecular sieves; benzyltrimethylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C 9.1: 97 percent / aq. HCl / methanol / 2.5 h / 0 - 20 °C View Scheme |
11β,17α-dihydoxy-21-iodopregna-1,4-diene-3,10-dione
rimexolone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: NaI; HOAc / acetone / Heating 2.1: 1.40 g / semicarbazide*HCl / H2O; acetic acid / 9.7 h / 80 - 85 °C 3.1: 1.42 g / DMAP; pyridine / 25 h 4.1: LiN(TMS)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.17 h / -65 - -60 °C 4.2: 82 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.03 h / -65 - 10 °C 5.1: 85.5 percent / CuCN / various solvent(s); tetrahydrofuran / 0.22 h / -45 °C 6.1: 63 percent / 4A molecular sieves; benzyltrimethylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C 7.1: 97 percent / aq. HCl / methanol / 2.5 h / 0 - 20 °C View Scheme |
11β,17-dihydroxy-21-(toluene-4-sulfonyloxy)-pregna-1,4-diene-3,20-dione
rimexolone
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: NaI / acetone / 20 °C 2.1: NaI; HOAc / acetone / Heating 3.1: 1.40 g / semicarbazide*HCl / H2O; acetic acid / 9.7 h / 80 - 85 °C 4.1: 1.42 g / DMAP; pyridine / 25 h 5.1: LiN(TMS)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.17 h / -65 - -60 °C 5.2: 82 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.03 h / -65 - 10 °C 6.1: 85.5 percent / CuCN / various solvent(s); tetrahydrofuran / 0.22 h / -45 °C 7.1: 63 percent / 4A molecular sieves; benzyltrimethylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C 8.1: 97 percent / aq. HCl / methanol / 2.5 h / 0 - 20 °C View Scheme |
11β,17α-dihydroxypregna-1,4-diene-3,20-dione
rimexolone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 1.40 g / semicarbazide*HCl / H2O; acetic acid / 9.7 h / 80 - 85 °C 2.1: 1.42 g / DMAP; pyridine / 25 h 3.1: LiN(TMS)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.17 h / -65 - -60 °C 3.2: 82 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.03 h / -65 - 10 °C 4.1: 85.5 percent / CuCN / various solvent(s); tetrahydrofuran / 0.22 h / -45 °C 5.1: 63 percent / 4A molecular sieves; benzyltrimethylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C 6.1: 97 percent / aq. HCl / methanol / 2.5 h / 0 - 20 °C View Scheme |
11β-hydroxy-1,4,16-trienepregna-3,20-dione
rimexolone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 1.42 g / DMAP; pyridine / 25 h 2.1: LiN(TMS)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.17 h / -65 - -60 °C 2.2: 82 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.03 h / -65 - 10 °C 3.1: 85.5 percent / CuCN / various solvent(s); tetrahydrofuran / 0.22 h / -45 °C 4.1: 63 percent / 4A molecular sieves; benzyltrimethylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C 5.1: 97 percent / aq. HCl / methanol / 2.5 h / 0 - 20 °C View Scheme |
11β-(trimethylsiloxy)-pregna-1,4,16-trien-3,20-dione
rimexolone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: LiN(TMS)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.17 h / -65 - -60 °C 1.2: 82 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.03 h / -65 - 10 °C 2.1: 85.5 percent / CuCN / various solvent(s); tetrahydrofuran / 0.22 h / -45 °C 3.1: 63 percent / 4A molecular sieves; benzyltrimethylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C 4.1: 97 percent / aq. HCl / methanol / 2.5 h / 0 - 20 °C View Scheme |
21-methyl-11β-(trimethylsiloxy)-pregna-1,4,16-trien-3,20-dione
rimexolone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 85.5 percent / CuCN / various solvent(s); tetrahydrofuran / 0.22 h / -45 °C 2: 63 percent / 4A molecular sieves; benzyltrimethylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C 3: 97 percent / aq. HCl / methanol / 2.5 h / 0 - 20 °C View Scheme |
16α,21-dimethyl-11β,20-bis(trimethylsiloxy)-pregna-1,4,17(20)-trien-3-one
rimexolone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 63 percent / 4A molecular sieves; benzyltrimethylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C 2: 97 percent / aq. HCl / methanol / 2.5 h / 0 - 20 °C View Scheme |
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