20-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,3beta,7alpha-tris(methoxycarbonyloxy)pregn-5-ene → 21,21-Dimethoxy-20-methylpregn-5-ene-1alpha,3beta,7alpha-triol

HRID 1708812Notes

Reaction equation

HRID 1708812 reaction equation
C([O:9][C@H:10]1[CH2:33][C@H:32]([O:34]C(=O)NC)[C@@:31]2([CH3:39])[C:12](=[CH:13][C@@H:14]([O:41]C(OC)=O)[C@@H:15]3[C@@H:30]2[CH2:29][CH2:28][C@@:27]2([CH3:40])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[CH:20]([CH3:26])[CH:21]([O:24][CH3:25])[O:22][CH3:23])[CH2:11]1)(=O)C1C=CC=CC=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>>[CH3:25][O:24][CH:21]([O:22][CH3:23])[CH:20]([CH3:26])[C@@H:19]1[C@:27]2([CH3:40])[C@H:16]([C@H:15]3[C@H:30]([CH2:29][CH2:28]2)[C@:31]2([CH3:39])[C:12]([CH2:11][C@@H:10]([OH:9])[CH2:33][C@@H:32]2[OH:34])=[CH:13][C@H:14]3[OH:41])[CH2:17][CH2:18]1

Participants

3

Reactant 2

HCID 5714185820-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,3beta,7alpha-tris(methoxycarbonyloxy)pregn-5-eneHCID 678529553beta-benzoyloxy-21,21-dimethoxy-20-methyl-1alpha-(N-methylcarbamoyl)oxy-7alpha-(methoxycarbonyl)oxypregn-5-ene

Product 1

HCID 6785299121,21-Dimethoxy-20-methylpregn-5-ene-1alpha,3beta,7alpha-triolYield 81.3%

Procedure

The reaction and workup procedures of Example 140 were repeated except that 85 mg of 3β-benzoyloxy-21,21-dimethoxy-20-methyl-1α-(N-methylcarbamoyl)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 45 mg of 21,21-dimethoxy-20-methylpregn-5-ene-1α,3β,7α-triol showing the following physical properties.

Workup

  1. customThe reaction and workup procedures of Example 140

Sources & evidence

ORD record
ord-057729f206bc4342a66bdc122a3c0543
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

Loading…