Potassium sodium tartarate → N-(4-(4-(Ethyl(2-cyclopentylethyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide

HRID 1654291Notes

Reaction equation

HRID 1654291 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:9]([C:26](=O)[CH2:27][CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)[CH2:10][CH2:11][CH2:12][CH:13]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][CH:16]=1)[OH:14])[CH3:8].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1>[CH2:7]([N:9]([CH2:26][CH2:27][CH:28]1[CH2:29][CH2:30][CH2:31][CH2:32]1)[CH2:10][CH2:11][CH2:12][CH:13]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH3:25])(=[O:23])=[O:24])=[CH:17][CH:16]=1)[OH:14])[CH3:8]

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 20080112N-(4-(4-(ethyl(cyclopentylacetyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 15294454N-(4-(4-(Ethyl(2-cyclopentylethyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamideYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A 1M solution of LiAlH4 in THF (15.9 ml) was mixed with THF (15.9 ml) and cooled, under nitrogen in an ice bath. To this solution was added, dropwise, with stirring, a solution of the product from Step I (3.0 g, 0.0076 mol) in THF (30.7 ml). The mixture was kept in the ice bath for 1 hour and then treated cautiously with a saturated potassium sodium tartrate solution (16.1 ml). This mixture was stirred at ambient temperature for 45 minutes and extracted with EtOAc. The extract was washed with water, dried (MgSO4) and concentrated. The residue was chromatographed on silica gel with 10-20% MeOH--CHCl3. A solution of the product in Et2O was washed with NaHCO3 and concentrated to give 1.86 g of the titled compound which is a compound of Formula I'. The mass spectrum had m/z 382 (M+). Theory for C20H34N2O3S: 382.2290; measured: 382.2291.

Workup

  1. temperaturecooled, under nitrogen in an ice bath
  2. additionTo this solution was added
  3. stirringThis mixture was stirred at ambient temperature for 45 minutes
  4. extractionextracted with EtOAc
  5. washThe extract was washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel with 10-20% MeOH
  9. washA solution of the product in Et2O was washed with NaHCO3
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-2fda4775f84c4779be76f778d2ed894c
Source dataset
uspto-grants-1995_04
Patent number
US05405997

Reaction notes

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