Potassium trimethylsilanolate → (1R)-2-(6-(2-((2,6-dichlorophenyl)methoxy)ethoxy)hexylamino)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

HRID 2116945Notes

Reaction equation

HRID 2116945 reaction equation
[Cl:1][C:2]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:3]=1[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:19][C@@H:18]([C:20]2[CH:31]=[CH:30][C:23]3[O:24][C:25]([CH3:29])([CH3:28])[O:26][CH2:27][C:22]=3[CH:21]=2)[O:17]C1=O.C[Si](C)(C)[O-].[K+]>C1COCC1>[Cl:1][C:2]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:3]=1[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:19][C@@H:18]([C:20]1[CH:31]=[CH:30][C:23]2[O:24][C:25]([CH3:28])([CH3:29])[O:26][CH2:27][C:22]=2[CH:21]=1)[OH:17]

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 46833391(5R)-3-(6-(2-((2,6-dichlorophenyl)methoxy)ethoxy)hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Product 1

HCID 46834265(1R)-2-(6-(2-((2,6-dichlorophenyl)methoxy)ethoxy)hexylamino)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanolYield 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (5R)-3-(6-{2-[(2,6-dichlorobenzyl)oxy]ethoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (140 mg) in THF (7 ml) under nitrogen was treated with potassium trimethylsilanolate (130 mg) and the mixture was heated (oil bath temperature 80°) with stirring for 3 h. The mixture was cooled to 20° and was partitioned between phosphate buffer solution (20 ml, pH6.5) and EtOAc (20 ml). The organic phase was separated, dried (NaSO4) and the solvent evaporated in vacuo to give the title compound (130 mg). LCMS RT=3.00 min.

Workup

  1. temperaturethe mixture was heated (oil bath temperature 80°)
  2. temperatureThe mixture was cooled to 20°
  3. customwas partitioned between phosphate buffer solution (20 ml, pH6.5) and EtOAc (20 ml)
  4. customThe organic phase was separated
  5. dry with materialdried (NaSO4)
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-f9fe374f0a964c348713ca47b374c1f7
Source dataset
uspto-grants-2008_10
Patent number
US07439393B2

Reaction notes

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