Water → HCID 19088496, compound

HRID 1463878Notes

Reaction equation

HRID 1463878 reaction equation
[CH2:1]([N:8]([C:10]([CH3:18])([CH3:17])[CH2:11][C:12](OCC)=[O:13])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:1]([N:8]([C:10]([CH3:18])([CH3:17])[CH2:11][CH2:12][OH:13])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19088497HCID 19088497, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19088496HCID 19088496, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 3-(N-benzyl-N-methylamino)-3-methylbutanoate (23.6 g--see Preparation 9) in anhydrous tetrahydrofuran (100 ml) was added, dropwise, over 20 minutes to a stirred suspension of lithium aluminium hydride (7.2 g) in anhydrous tetrahydrofuran (300 ml). When the addition was complete, the mixture was stirred at room temperature for 3 hours. Water (7 ml) was carefully added dropwise followed by 15% aqueous sodium hydroxide (7 ml) and finally more water (20 ml). The resulting solid precipitate was filtered off and washed with ethyl acetate (3×50 ml). The filtrate and washings were combined and concentrated in vacuo to give the title compound as a colourless, mobile oil, yield 19.00 g.

Workup

  1. additionWhen the addition
  2. filtrationThe resulting solid precipitate was filtered off
  3. washwashed with ethyl acetate (3×50 ml)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3bb66235341743b88cd48f23a87093e8
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

Loading…