Diisobutylaluminumhydride → 20-(1,3-Dioxolan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3alpha-ol

HRID 1708792Notes

Reaction equation

HRID 1708792 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:28])[C@@H:18]4[O:27][C@@H:19]42)[CH:14]=[CH:13]3)[CH2:10][CH2:9]1)[CH3:7].[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1.C1(C)C=CC=CC=1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C@H:17]([OH:28])[C@@H:18]4[O:27][C@@H:19]42)[CH:14]=[CH:13]3)[CH2:10][CH2:9]1)[CH3:7]

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 8674581520-(1,3-Dioxolan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3-one

Product 1

HCID 8674582820-(1,3-Dioxolan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3alpha-olYield 80%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 200 ml of tetrahydrofuran was dissolved 11.7 g of 20-(1,3-dioxolan-2-yl)-1α,2α-epoxypregna-4,6-dien-3-one, followed by addition of 36 ml of a 1.0M solution of diisobutylaluminum hydride in toluene under ice-cooling. The mixture was stirred under ice-cooling for 15 minutes. Then, the reaction mixture was worked up in the same manner as Example 68 to recover 9.4 g of 20-(1,3-dioxolan-2-yl)-1α,2α-epoxypregna-4,6-dien-3α-ol (yield: 80%) showing the following physical properties.

Workup

  1. temperaturecooling
  2. temperaturecooling for 15 minutes

Sources & evidence

ORD record
ord-11523d4d48894f7193c6c7a73181864b
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

Loading…