Sodium triethylboranuide → 1alpha,2alpha-Epoxy-21,21-dimethoxy-20-methylpregna-4,6-dien-3alpha-ol

HRID 1196360Notes

Reaction equation

HRID 1196360 reaction equation
[O:1]1[C@H:3]2[C:4](=[O:28])[CH:5]=[C:6]3[C@:25]([CH3:26])([C@@H:2]12)[C@@H:24]1[C@H:9]([C@H:10]2[C@:21]([CH3:27])([CH2:22][CH2:23]1)[C@@H:13]([CH:14]([CH3:20])[CH:15]([O:18][CH3:19])[O:16][CH3:17])[CH2:12][CH2:11]2)[CH:8]=[CH:7]3.C([BH-](CC)CC)C.[Na+]>O1CCCC1>[O:1]1[C@H:3]2[C@@H:4]([OH:28])[CH:5]=[C:6]3[C@:25]([CH3:26])([C@@H:2]12)[C@@H:24]1[C@H:9]([C@H:10]2[C@:21]([CH3:27])([CH2:22][CH2:23]1)[C@@H:13]([CH:14]([CH3:20])[CH:15]([O:18][CH3:19])[O:16][CH3:17])[CH2:12][CH2:11]2)[CH:8]=[CH:7]3

Participants

4

Reactant 2

HCID 5129078Sodium triethylboranuideHCID 540033941alpha,2alpha-Epoxy-21,21-dimethoxy-20-methylpregna-4,6-dien-3-one

Product 1

HCID 867458291alpha,2alpha-Epoxy-21,21-dimethoxy-20-methylpregna-4,6-dien-3alpha-olYield 86.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 200 ml of tetrahydrofuran was dissolved 11.8 g of 1α,2α-epoxy-21,21-dimethoxy-20-methylpregna-4,6-dien-3-one, followed by addition of 36 ml of a 1.0M solution of sodium triethylborohydride in tetrahydrofuran under ice-cooling. The mixture was stirred under ice-cooling for 15 minutes, after which it was worked up in the same manner as Example 68 to give 10.24 g of 1α,2α-epoxy-21,21-dimethoxy-20-methylpregna-4,6-dien-3α-ol (yield: 85%) showing the following physical properties.

Workup

  1. temperaturecooling
  2. temperaturecooling for 15 minutes

Sources & evidence

ORD record
ord-3725eac52d6e41318419b34f33ec4de0
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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