Sodium p-toluenesulfinate → 20-Methyl-1alpha,3beta-bis(methoxymethoxy)-21-p-tolylsulfonylpregna-5,7-diene
Reaction equation
Br[CH2:2][CH:3]([CH3:31])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C:11]([CH2:12][C@@H:13]([O:27][CH2:28][O:29][CH3:30])[CH2:14][C@@H:15]2[O:23][CH2:24][O:25][CH3:26])=[CH:10][CH:9]=3)[CH2:6][CH2:5]1.[C:32]1([CH3:41])[CH:37]=[CH:36][C:35]([S:38]([O-:40])=[O:39])=[CH:34][CH:33]=1.[Na+].BrCC(C)[C@@H]1[C@]2(C)[C@H](C3[C@H](CC2)[C@]2(C)C(C[C@@H](OC(OC)=O)C[C@@H]2OC(OC)=O)=CC=3)CC1.C1(S([O-])=O)C=CC=CC=1.[Na+]>>[CH3:31][CH:3]([C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C:11]([CH2:12][C@@H:13]([O:27][CH2:28][O:29][CH3:30])[CH2:14][C@@H:15]2[O:23][CH2:24][O:25][CH3:26])=[CH:10][CH:9]=3)[CH2:6][CH2:5]1)[CH2:2][S:38]([C:35]1[CH:36]=[CH:37][C:32]([CH3:41])=[CH:33][CH:34]=1)(=[O:40])=[O:39]Participants
5
Reactant 4
Product 1
Procedure
The procedure of Example 5 was repeated except that 59 mg of 21-bromo-20-methyl-1α,3β-bis(methoxymethoxy)pregna-5,7-diene and 95 mg of sodium p-toluenesulfinate were used in lieu of 65 mg of 21-bromo-20-methyl-1α,3β-bis(methoxycarbonyloxy) pregna-5,7-diene and 80 mg of sodium benzenesulfinate, respectively, to give 43 mg of 20-methyl-1α,3β-bis(methoxymethoxy)-21-p-tolylsulfonylpregna-5,7-diene.
Sources & evidence
- ORD record
- ord-6acfa0996b3b49678a4c8240d84bc310
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05218109
Reaction notes
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