Potassium trimethylsilanolate → (1R)-2-[(6-{4-[3-(Cyclopentylsulfinyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

HRID 2118324Notes

Reaction equation

HRID 2118324 reaction equation
[CH:1]1([S:6]([C:8]2[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]3[CH2:29][C@@H:28]([C:30]4[CH:41]=[CH:40][C:33]5[O:34][C:35]([CH3:39])([CH3:38])[O:36][CH2:37][C:32]=5[CH:31]=4)[O:27]C3=O)[CH:11]=[CH:12][CH:13]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si](C)(C)[O-].[K+]>O1CCCC1>[CH:1]1([S:6]([C:8]2[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][CH2:29][C@@H:28]([C:30]3[CH:41]=[CH:40][C:33]4[O:34][C:35]([CH3:38])([CH3:39])[O:36][CH2:37][C:32]=4[CH:31]=3)[OH:27])[CH:11]=[CH:12][CH:13]=2)=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 69119380(5R)-3-(6-{4-[3-(Cyclopentylsulfinyl)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Product 1

HCID 69119885(1R)-2-[(6-{4-[3-(Cyclopentylsulfinyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanolYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of (5R)-3-(6-{4-[3-(cyclopentylsulfinyl)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (0.14 g) and potassium trimethyl silanolate (0.45 g) in tetrahydrofuran (10 ml) was heated to reflux for 2 h. The mixture was poured into phoshate buffer solution (pH 5, 50 ml) and extracted into ethyl acetate. The extracts were washed with water, dried (Na2SO4) and evaporated. The residual oil was purified on a biotage cartridge (8 g) using dichloromethane-ethanol-0.88 ammonia (100:8:1) as eluent. The appropriate fractions were evaporated to give the title compound (0.11 g) LCMS RT=2.89 min.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. extractionextracted into ethyl acetate
  4. washThe extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residual oil was purified on a biotage cartridge (8 g)
  8. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-dd5b4e1fab2245d59fce3eec26043ae6
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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