1alpha,3beta-Bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehyde → 1alpha,3beta-Bis(t-butyldimethylsilyloxy)-20-methylpregna-5,7-dien-21-ol

HRID 1587613Notes

Reaction equation

HRID 1587613 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@:29]2([CH3:30])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:31])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[CH:21]([CH:23]=[O:24])[CH3:22])[CH2:12][C@@H:11]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].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>>[Si:1]([O:8][C@@H:9]1[C@@:29]2([CH3:30])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:31])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[CH:21]([CH3:22])[CH2:23][OH:24])[CH2:12][C@@H:11]([O:32][Si:33]([C:36]([CH3:37])([CH3:39])[CH3:38])([CH3:34])[CH3:35])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 543675231alpha,3beta-Bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehydeHCID 544259821alpha,3beta-Bis(t-butyldimethylsilyloxy)pregna-5,7-diene-20-carbaldehyde

Product 1

HCID 545720211alpha,3beta-Bis(t-butyldimethylsilyloxy)-20-methylpregna-5,7-dien-21-olYield 83.3%

Procedure

The procedure of Example 1 was repeated except that 110 mg of 1α,3β-bis(t-butyldimethylsilyloxy)pregna-5,7-diene-20-carbaldehyde was used in lieu of 100 mg of 1α,3β-bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehyde to give 92 mg of 1α,3β-bis(t-butyldimethylsilyloxy)-20-methylpregna-5,7-dien-21-ol.

Sources & evidence

ORD record
ord-dfb2a672cf784c1fba4efe2ddfa93249
Source dataset
uspto-grants-1993_06
Patent number
US05218109

Reaction notes

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