N,N-Dimethylglycine → (S)-4-[4-(4-Methoxyphenoxy)-benzyl]-2,2-dimethyl-oxazolidine-3carboxylic acid tert-butyl ester

HRID 1669515Notes

Reaction equation

HRID 1669515 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:11][O:10][C:9]1([CH3:22])[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].I[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1.CN(C)CC(O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.ClCCl>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)=[CH:18][CH:19]=2)[CH2:11][O:10][C:9]1([CH3:22])[CH3:21])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 10796Cesium carbonateHCID 696764-IodoanisoleHCID 10425336tert-Butyl (S)-4-(4-hydroxybenzyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Product 1

HCID 67351484(S)-4-[4-(4-Methoxyphenoxy)-benzyl]-2,2-dimethyl-oxazolidine-3carboxylic acid tert-butyl esterYield 51.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-4-(4-Hydroxy-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (150 mg, 0.5 mmol, 1 eq.)), 4-iodoanisole (180 mg, 0.75 mmol, 1.5 eq.) in dioxane (4 ml) was added CuI(I) (20 mg, 0.05 mmol, 0.1 eq.), N,N-dimethylglycine (30 mg, 0.15 mmol, 0.3 eq.) and cesium carbonate (500 mg, 1.5 mmol, 3 eq.). The resulting mixture was stirred under Ar at reflux overnight. After cooling to room temperature, the volatile material was removed under reduced pressure to give a residue, which was partitioned between water (10 ml) and ethyl acetate (10 ml). The ethyl acetate layer was separated and dried over anhydrous MgSO4. Evaporation of solvent under reduced pressure gave a residue, which was passed through a plug of silica gel using dichloromethane (50 ml) as eluent to give 106 mg of desired product (51% yield).

Workup

  1. temperatureat reflux overnight
  2. customthe volatile material was removed under reduced pressure
  3. customto give a residue, which
  4. customwas partitioned between water (10 ml) and ethyl acetate (10 ml)
  5. customThe ethyl acetate layer was separated
  6. dry with materialdried over anhydrous MgSO4
  7. customEvaporation of solvent under reduced pressure
  8. customgave a residue, which

Sources & evidence

ORD record
ord-68d7fd2f4fbd4aed8dc2786b191eb44b
Source dataset
uspto-grants-2011_08
Patent number
US07989480B2

Reaction notes

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