Hydrochloric Acid → 2-(1,2-Epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-chloromethyl-1,4-cyclohexanediol

HRID 1646630Notes

Reaction equation

HRID 1646630 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].[ClH: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][Cl:21])[OH:16])[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 222778FumagillolHCID 516892Sodium Bicarbonate

Product 1

HCID 198010732-(1,2-Epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-chloromethyl-1,4-cyclohexanediolYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of fumagillol (200 mg) in ethanol (2 ml) was added 0.5N hydrochloric acid (1 ml), and the mixture was stirred at room temperatures for one hour. To the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate to neutralize, which was concentrated under reduced pressure. The concentrate was purified by means of a silica gel column chromatography (carrier 10 g, developing solvent:hexane-ethylacetate=3:1) to give 2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-(chloromethyl)-1,4-cyclohexanediol (200 mg: yield 90%).

Workup

  1. concentrationwhich was concentrated under reduced pressure
  2. customThe concentrate was purified by means of a silica gel column chromatography (carrier 10 g, developing solvent:hexane-ethylacetate=3:1)

Sources & evidence

ORD record
ord-06e4d43607a54485961ab4f401c4f8bc
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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