Water → 3-Tetrahydropyranyloxyethyl-3-(3,4-dichlorophenyl)pyrrolidine

HRID 1080659Notes

Reaction equation

HRID 1080659 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]1([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[CH2:14][NH:13][C:12](=O)[CH2:11]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]1([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[CH2:11][CH2:12][NH:13][CH2:14]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 211976714-(2-Tetrahydropyranyloxyethyl)-4-(3,4-dichlorophenyl)-2-pyrrolidoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 211976873-Tetrahydropyranyloxyethyl-3-(3,4-dichlorophenyl)pyrrolidineYield 90.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

3.9 g of the 4-(2-tetrahydropyranyloxyethyl)-4-(3,4-dichlorophenyl)-2-pyrrolidone prepared above are dissolved in 50 ml of tetrahydrofuran and the solution is added to a suspension of 0.9 g of lithium aluminum hydride in 5 ml of THF heated to 60° C. The reaction mixture is heated for one hour at 60° C. and then cooled. 1 ml of water, 1 ml of 4N sodium hydroxide and 3 ml of water are added. The inorganic material is filtered off and the filtrate is concentrated under vacuum. The residue is taken up in ethyl ether, dried over MgSO4 and concentrated under vacuum to give 3.4 g of the expected product.

Workup

  1. temperatureThe reaction mixture is heated for one hour at 60° C.
  2. temperaturecooled
  3. filtrationThe inorganic material is filtered off
  4. concentrationthe filtrate is concentrated under vacuum
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-254c7aac416341a6928c97fd302e15a8
Source dataset
uspto-grants-1996_12
Patent number
US05583134

Reaction notes

Loading…