Hydrogen Bromide → HCID 19801027, compound

HRID 1646632Notes

Reaction equation

HRID 1646632 reaction equation
[CH3:1][C:2]([CH3:20])=[CH:3][CH2:4][C@H:5]1[O:7][C@@:6]1([C@@H:9]1[C@:14]2([O:16][CH2:15]2)[CH2:13][CH2:12][C@@H:11]([OH:17])[C@H:10]1[O:18][CH3:19])[CH3:8].[BrH:21].C(=O)([O-])O.[Na+]>C(O)C>[O:7]1[CH:5]([CH2:4][CH:3]=[C:2]([CH3:20])[CH3:1])[C:6]1([CH:9]1[CH:10]([O:18][CH3:19])[CH:11]([OH:17])[CH2:12][CH2:13][C:14]1([CH2:15][Br:21])[OH:16])[CH3:8]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 222778FumagillolHCID 516892Sodium Bicarbonate

Product 1

HCID 19801027HCID 19801027, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of fumagillol (230 mg) in ethanol (2 ml) was added a 5% aqueous solution of hydrobromic acid (1 ml), and the mixture was stirred for one hour at room temperatures. The reaction mixture was neutralized with a saturated aqueous solution of sodium hydrogencarbonate, followed by concentration under reduced pressure. The concentrate was purified by means of a silica gel column chromatography (carrier 10 g, developing solvent: hexane-ethyl acetate=7:3) to afford 2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy1-bromomethyl-1,4-cyclohexanediol (242 mg: yield 80%) as a colorless oily product.

Workup

  1. concentrationfollowed by concentration under reduced pressure
  2. customThe concentrate was purified by means of a silica gel column chromatography (carrier 10 g, developing solvent: hexane-ethyl acetate=7:3)

Sources & evidence

ORD record
ord-1cfdfe59996e4df9ad00c05bb9584908
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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