Methyl 1alpha,3beta-bis(methoxycarbonyloxy)pregna-5,7-diene-20 carboxylate → 1alpha,3beta-Bis(methoxymethoxy)-20methylpregna-5,7-diene-21-ol

HRID 1587637Notes

Reaction equation

HRID 1587637 reaction equation
[CH3:1][O:2][CH2:3][O:4][C@@H:5]1[C@@:27]2([CH3:28])[C:9](=[CH:10][CH:11]=[C:12]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:29])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[CH:17]([C:19](OC)=[O:20])[CH3:18])[CH2:8][C@@H:7]([O:30][CH2:31][O:32][CH3:33])[CH2:6]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(OC)=O)C)C[C@@H](OC(OC)=O)C1)=O>>[CH3:1][O:2][CH2:3][O:4][C@@H:5]1[C@@:27]2([CH3:28])[C:9](=[CH:10][CH:11]=[C:12]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:29])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[CH:17]([CH3:18])[CH2:19][OH:20])[CH2:8][C@@H:7]([O:30][CH2:31][O:32][CH3:33])[CH2:6]1

Participants

3

Reactant 2

HCID 18652401Methyl 1alpha,3beta-bis(methoxycarbonyloxy)pregna-5,7-diene-20 carboxylateHCID 53799872Methyl 1alpha,3beta-bis(methoxymethoxy)pregna-5,7-diene-20-carboxylate

Product 1

HCID 186523871alpha,3beta-Bis(methoxymethoxy)-20methylpregna-5,7-diene-21-olYield 77%

Procedure

The procedure of Example 11 was repeated except that 65 mg of methyl 1α,3β-bis(methoxymethoxy)pregna-5,7-diene-20-carboxylate was used in lieu of 70 mg of methyl 1α,3β-bis(methoxycarbonyloxy)pregna-5,7-diene-20 carboxylate to give 47 mg of 1α,3β-bis(methoxymethoxy)-20methylpregna-5,7-diene-21-ol, whose 1H NMR spectrum was identical with that obtained in Example 10.

Sources & evidence

ORD record
ord-ef995da422d84290a8e11c007996f4c3
Source dataset
uspto-grants-1993_06
Patent number
US05218109

Reaction notes

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