20-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha-(tert-butyldimethylsilyl)oxy-3beta-(N,N-dimethylcarbamoyl)oxy-7alpha-(methoxycarbonyl)oxypregn-5-ene → 20-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha-(tert-butyldimethylsilyl)oxypregn-5-ene-3beta,7alpha-diol

HRID 1196376Notes

Reaction equation

HRID 1196376 reaction equation
[CH3:1][C:2]1([CH3:48])[CH2:7][O:6][CH:5]([CH:8]([C@@H:10]2[C@:27]3([CH3:28])[C@H:13]([C@H:14]4[C@H:24]([CH2:25][CH2:26]3)[C@:22]3([CH3:23])[C:17]([CH2:18][C@@H:19]([O:37]C(=O)N(C)C)[CH2:20][C@@H:21]3[O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])=[CH:16][C@H:15]4[O:43]C(OC)=O)[CH2:12][CH2:11]2)[CH3:9])[O:4][CH2:3]1.CC1(C)COC(C([C@@H]2[C@]3(C)[C@H]([C@H]4[C@H](CC3)[C@]3(C)C(C[C@@H](OC(OC)=O)C[C@@H]3OC(OC)=O)=C[C@H]4OC(OC)=O)CC2)C)OC1>>[CH3:48][C:2]1([CH3:1])[CH2:7][O:6][CH:5]([CH:8]([C@@H:10]2[C@:27]3([CH3:28])[C@H:13]([C@H:14]4[C@H:24]([CH2:25][CH2:26]3)[C@:22]3([CH3:23])[C:17]([CH2:18][C@@H:19]([OH:37])[CH2:20][C@@H:21]3[O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])=[CH:16][C@H:15]4[OH:43])[CH2:12][CH2:11]2)[CH3:9])[O:4][CH2:3]1

Participants

3

Reactant 2

HCID 2284392520-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha-(tert-butyldimethylsilyl)oxy-3beta-(N,N-dimethylcarbamoyl)oxy-7alpha-(methoxycarbonyl)oxypregn-5-eneHCID 5714185820-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,3beta,7alpha-tris(methoxycarbonyloxy)pregn-5-ene

Product 1

HCID 6785287120-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha-(tert-butyldimethylsilyl)oxypregn-5-ene-3beta,7alpha-diolYield 71.2%

Procedure

The reaction and workup procedures of Example 140 were repeated except that 95 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α-(tert-butyldimethylsilyl)oxy-3β-(N,N-dimethylcarbamoyl)oxy-7α-(methoxycarbonyl)oxypregn-5-ene was used in lieu of 100 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,3β,7α-tris(methoxycarbonyloxy)pregn-5-ene to give 55 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α-(tert-butyldimethylsilyl)oxypregn-5-ene-3β,7α-diol showing the following physical properties.

Workup

  1. customThe reaction and workup procedures of Example 140

Sources & evidence

ORD record
ord-929e026033cc4a56ab5e23649e265f78
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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