1alpha,3beta-Bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehyde → 21,21-Dimethoxy-20-methylpregna-5,7-diene-1alpha,3betadiol

HRID 1708822Notes

Reaction equation

HRID 1708822 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][CH:14]=[C: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.COC(O[C@@H]1[C@@]2(C)C(=CC=C3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2C(C=O)C)C[C@@H](OC(OC)=O)C1)=O>>[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: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][CH:14]=3)[CH2:17][CH2:18]1

Participants

3

Reactant 2

HCID 543675231alpha,3beta-Bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehydeHCID 678529803beta-benzoyloxy-21,21-dimethoxy-20-methyl-1alpha-(N-methylcarbamoyl)oxypregna-5,7-diene

Product 1

HCID 5718934321,21-Dimethoxy-20-methylpregna-5,7-diene-1alpha,3betadiolYield 91.8%

Procedure

The reaction and workup procedures of Example 164 were repeated except that 100 mg of 3β-benzoyloxy-21,21-dimethoxy-20-methyl-1α-(N-methylcarbamoyl)oxypregna-5,7-diene was used in lieu of 100 mg of 1α,3β-bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehyde to give 65 mg of 21,21-dimethoxy-20-methylpregna-5,7-diene-1α,3β-diol showing the following physical properties.

Workup

  1. customThe reaction and workup procedures of Example 164

Sources & evidence

ORD record
ord-f5bb37c6a4af4fd2bd56208811bc02aa
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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