20-(1,3-Dioxolan-2-yl)-1alpha-acetoxy-3beta-(methoxymethyl)oxypregna-5,7-diene → 1alpha-Acetoxy-3beta-(methoxymethyl)oxypregna-5,7-diene-20carbaldehyde

HRID 1708819Notes

Reaction equation

HRID 1708819 reaction equation
[O:1]1CCO[CH:2]1[CH:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15]([CH2:16][C@@H:17]([O:31][CH2:32][O:33][CH3:34])[CH2:18][C@@H:19]2[O:27][C:28](=[O:30])[CH3:29])=[CH:14][CH:13]=3)[CH2:10][CH2:9]1)[CH3:7]>CC(C)=O.Cl(O)(=O)(=O)=O>[C:28]([O:27][C@@H:19]1[C@@:20]2([CH3:21])[C:15](=[CH:14][CH:13]=[C:12]3[C@@H:22]2[CH2:23][CH2:24][C@@:25]2([CH3:26])[C@H:11]3[CH2:10][CH2:9][C@@H:8]2[CH:6]([CH:2]=[O:1])[CH3:7])[CH2:16][C@@H:17]([O:31][CH2:32][O:33][CH3:34])[CH2:18]1)(=[O:30])[CH3:29]

Participants

4

Reactant 1

HCID 6785294320-(1,3-Dioxolan-2-yl)-1alpha-acetoxy-3beta-(methoxymethyl)oxypregna-5,7-diene

Product 1

HCID 228438981alpha-Acetoxy-3beta-(methoxymethyl)oxypregna-5,7-diene-20carbaldehydeYield 44.1%

Reagents, catalysts & solvents 2

HCID 24247Perchloric AcidCatalystHCID 180AcetoneSolvent

Procedure

In 10 ml of acetone was dissolved 100 mg of 20-(1,3-dioxolan-2-yl)-1α-acetoxy-3β-(methoxymethyl)oxypregna-5,7-diene, followed by addition of one drop of 70% perchloric acid, and the mixture was refluxed in an atmosphere of argon gas for 2 hours. The reaction mixture was then worked up in the same manner as Example 156 to give 40 mg of 1α-acetoxy-3β-(methoxymethyl)oxypregna-5,7-diene-20-carbaldehyde showing the following physical properties. 1H-NMR spectrum (90 MHz) δTMSCDCl 3: 0.66 (s, 3H), 1.00 (s, 3H), 1.16 (d, J=6.2 Hz, 3H), 2.07 (s, 3H), 3.35 (s, 3H), 4.30 (m, 1H), 4.65 (br. s, 2H), 4.99 (1H), 5.35 (m, 1H), 5.70 (m, 1H), 9.57 (d, J=3.5 Hz, 1 H) IR spectrum (KBr): 1735, 1725 cm-1

Workup

  1. temperaturethe mixture was refluxed in an atmosphere of argon gas for 2 hours

Sources & evidence

ORD record
ord-870afdc0f13147b387f147a6bd7c63c9
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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