20-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxy-7alpha-(N-methylcarbamoyloxy)pregn-5-en3beta-ol → 1alpha,2alpha-epoxy-3beta-hydroxy-7alpha-(N-methylcarbamoyloxy)pregn-5-ene-20-carbaldehyde

HRID 1708772Notes

Reaction equation

HRID 1708772 reaction equation
CC1(C)CO[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:30])[C@@H:20]5[O:29][C@@H:21]53)=[CH:16][C@H:15]4[O:31][C:32](=[O:35])[NH:33][CH3:34])[CH2:12][CH2:11]2)[CH3:9])[O:4]C1.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](O)[C@@H]5O[C@@H]53)=C[C@H]4O)CC2)C)OC1>>[O:29]1[C@H:20]2[C@H:19]([OH:30])[CH2:18][C:17]3[C@:22]([CH3:23])([C@@H:21]12)[C@@H:24]1[C@H:14]([C@H:13]2[C@:27]([CH3:28])([CH2:26][CH2:25]1)[C@@H:10]([CH:8]([CH:5]=[O:4])[CH3:9])[CH2:11][CH2:12]2)[C@H:15]([O:31][C:32](=[O:35])[NH:33][CH3:34])[CH:16]=3

Participants

3

Reactant 2

HCID 5705512720-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxy-7alpha-(N-methylcarbamoyloxy)pregn-5-en3beta-olHCID 8674580820-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregn-5-ene-3beta,7alpha-diol

Product 1

HCID 884637211alpha,2alpha-epoxy-3beta-hydroxy-7alpha-(N-methylcarbamoyloxy)pregn-5-ene-20-carbaldehydeYield 62.7%

Procedure

The procedure of Example 36 was repeated except that 2.5 mg (0. 005 mmole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxy-7α-(N-methylcarbamoyloxy)pregn-5-en-3β-ol was used in lieu of 2.2 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregn-5-ene-3β,7α-diol to give 1.3 mg of 1α,2α-epoxy-3β-hydroxy-7α-(N-methylcarbamoyloxy)pregn-5-ene-20-carbaldehyde (yield: 62%).

Sources & evidence

ORD record
ord-63be71f0a7f34e9f974196e566c0e8c5
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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