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

HRID 2118327Notes

Reaction equation

HRID 2118327 reaction equation
[CH:1]1([S:6]([C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:30][C@@H:29]([C:31]4[CH:42]=[CH:41][C:34]5[O:35][C:36]([CH3:40])([CH3:39])[O:37][CH2:38][C:33]=5[CH:32]=4)[O:28]C3=O)[CH:12]=[CH:13][CH:14]=2)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si](C)(C)[O-].[K+]>C1COCC1>[CH:1]1([S:6]([C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:30][C@@H:29]([C:31]3[CH:42]=[CH:41][C:34]4[O:35][C:36]([CH3:39])([CH3:40])[O:37][CH2:38][C:33]=4[CH:32]=3)[OH:28])[CH:12]=[CH:13][CH:14]=2)(=[O:8])=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 69119376(5R)-3-(6-{4-[3-(Cyclopentylsulfonyl)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Product 1

HCID 69119807(1R)-2-[(6-{4-[3-(Cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of (5R)-3-(6-{4-[3-(Cyclopentylsulfonyl)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one and potassium trimethyl silanolate (240 mg) in THF (6 ml) was heated to reflux for 1.5 h. The mixture was poured into phoshate buffer solution (pH 5) and extracted into DCM. The extracts were washed with water, dried (Na2SO4) and evaporated to give the title compound (120 mg). LCMS RT=2.93 min.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 h
  3. extractionextracted into DCM
  4. washThe extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-dffb7638fad8491c9a592050eb473ff8
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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