1,2-Dimethoxyethane → HCID 67073058, compound

HRID 2253038Notes

Reaction equation

HRID 2253038 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17](Br)[CH:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO[CH2:26][CH2:27]OC.[Cl-].[Li+].C([Sn](CCCC)(CCCC)C=C)CCC.[OH-].[Na+]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([CH:26]=[CH2:27])[CH:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 5

HCID 80711,2-DimethoxyethaneHCID 14798Sodium HydroxideHCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 67073333HCID 67073333, compound

Product 1

HCID 67073058HCID 67073058, compoundYield 83%

Procedure

To the solution of 0.5 g (1.3 mmol) (R)-2-(3-bromo-4-methoxy-benzyl)-morpholine-4-carboxylic acid tert-butyl ester (see Example 9) in 15 mL 1,2-dimethoxyethane 45 mg (39 μmol) tetrakis(triphenylphosphine)palladium(0) and 0.17 g (3.9 mmol) lithium chloride were added. After the addition of 0.45 mL tributyl(vinyl)tin the reaction was stirred under reflux for 23 h. After cooling down to room temperature the reaction suspension was poured on 1N aqueous sodium hydroxide solution and was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was chromatographed using MPLC and tert-butyl methyl ether: n-heptane (1:1 v/v) as eluant to give the compound as a colorless oil (83%).

Workup

  1. temperatureunder reflux for 23 h
  2. extractionwas extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed

Sources & evidence

ORD record
ord-69308f76bcdc4b77a0936b2109a793a5
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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