HCID 16049965, compound → HCID 68295550, compound

HRID 572478Notes

Reaction equation

HRID 572478 reaction equation
[OH:1][C@H:2]([CH2:15][OH:16])[C:3]#[C:4][C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8].[BrH:17].C1(NC2CCCCC2)CCCCC1>ClCCCl.CCOC(C)=O.[Cu](Br)Br>[Br:17][C:4]1[C:5]2[C:6](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:7](=[O:9])[O:8][C:3]=1[C@H:2]([OH:1])[CH2:15][OH:16]

Participants

6

Reactant 2

HCID 16049965HCID 16049965, compoundHCID 68295599HCID 68295599, compound

Product 1

HCID 68295550HCID 68295550, compoundYield 309.3%

Reagents, catalysts & solvents 3

HCID 24611Copper bromide (CuBr2)CatalystHCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of methyl 2-[(3S)-3,4-dihydroxy-1-butyn-1-yl]benzoate (500 mg, 2.270 mmol) in 1,2-Dichloroethane (DCE) (22 mL) was treated with dicyclohexylamine HBr (59.5 mg, 0.227 mmol) and then copper (II) bromide (1014 mg, 4.54 mmol) and stirred at 80° C. After 1.5 h, the reaction mixture was diluted with EtOAc, filtered through Celite and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate-hexanes 0-70%) to afford the title compound (200 mg, 0.702 mmol, 31% yield) as brown solid: Rt=0.46 min,

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel chromatography (ethyl acetate-hexanes 0-70%)

Sources & evidence

ORD record
ord-bf17e1a362ca4d0ca926e7041a7e8039
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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