Water → HCID 23294457, compound

HRID 1955181Notes

Reaction equation

HRID 1955181 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][C:30](OCC)=[O:31])[CH:24]=2)[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[CH2:7]([CH:14]1[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][CH2:30][OH:31])[CH:24]=2)[CH2:18][CH2:19]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23294330HCID 23294330, compound

Product 1

HCID 23294457HCID 23294457, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (150 mg, 4.0 mmol) in 10 mL of anhydrous THF was added dropwise a solution of 4-benzyl-1-(2-(3-(ethoxycarbonylmethyl)phenoxy)ethyl)piperidine (0.382 g, 1.00 mmol) in 2 mL of THF at -78° C. The resulting mixture was allowed to warm to room temperature and was stirred for 12 hr. Water (0.2 mL), 15% NaOH aqueous solution (0.2 mL) and water (1 mL) were added successively. The colorless solid was removed by filtration and washed with EtOAc (3×20 mL). The filtrate was dried over Na2SO4. Evaporation of solvents gave a residue, which was purified by flash chromatography giving the title product as colorless oil (223 mg, 66%) 1H NMR (CDCl3) 1.37 (m, 2 H), 1.60 (m, 1 H), 1.63 (m, 2 H), 2.05 (m, 2 H), 2.36 (d, J=6.6 Hz, 2 H), 2.76 (m, 2 H), 2.82 (m, 2 H), 2.95 (m, 3 H), 3.81 (t, J=6.9 Hz, 2 H), 4.08 (t, J=6.9 Hz, 2 H), 6.80 (m, 3 H), 7.17-7.29 (m, 6 H).

Workup

  1. customThe colorless solid was removed by filtration
  2. washwashed with EtOAc (3×20 mL)
  3. dry with materialThe filtrate was dried over Na2SO4
  4. customEvaporation of solvents
  5. customgave a residue, which
  6. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-1b4dd10d98f7443a932ed23db1680de0
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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