(R)-4-(Oxiran-2-ylmethoxy)benzonitrile → 4-[3-[ethyl[3-((S*)-propylsulfinyl)propyl]amino]-2(R)-hydroxypropoxy]-benzonitrile

HRID 345141Notes

Reaction equation

HRID 345141 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][CH2:6][S@:7]([CH2:9][CH2:10][CH3:11])=[O:8])[CH3:2].[O:12]1[CH2:14][C@@H:13]1[CH2:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1>C(O)(C)C>[CH2:1]([N:3]([CH2:4][CH2:5][CH2:6][S@:7]([CH2:9][CH2:10][CH3:11])=[O:8])[CH2:14][C@@H:13]([OH:12])[CH2:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6934186(R)-4-(Oxiran-2-ylmethoxy)benzonitrileHCID 86745130ethyl(3-(S*)-propylsulfinyl)propylamine

Product 1

HCID 545546274-[3-[ethyl[3-((S*)-propylsulfinyl)propyl]amino]-2(R)-hydroxypropoxy]-benzonitrileYield 102.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 3 g of ethyl(3-(S*)-propylsulfinyl)propylamine and 3.18 g of (R)-4-(oxiranylmethoxy)-benzonitrile was refluxed for 16 h in 25 ml of isopropyl alcohol. After evaporation of the solvent, the crude product was dissolved in 2M hydrochloric acid, washed with ether, the solution brought to pH 11.5 with 2M sodium hydroxide and extracted with dichloromethane. Evaporation of the organic phase gave 6.11 g of an oil.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe crude product was dissolved in 2M hydrochloric acid
  3. washwashed with ether
  4. extractionextracted with dichloromethane
  5. customEvaporation of the organic phase

Sources & evidence

ORD record
ord-4df32e244fb6403699c3c1723176931d
Source dataset
uspto-grants-1991_10
Patent number
US05055490

Reaction notes

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