Water → HCID 22594646, compound

HRID 1978309Notes

Reaction equation

HRID 1978309 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH2:12][C:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH:18]=1)=O)C.C(OCC)(=O)C.O>C(OCC)C.O1CCCC1>[OH:9][CH2:10][CH2:12][C:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 9970303Ethyl 1-[(1,1-dimethylethoxy)carbonyl]-3,6-dihydro-4(2H)-pyridineacetateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 22594646HCID 22594646, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.66 g (17.5 mM) of lithium aluminum hydride in 100 ml of diethyl ether was added a solution of 4.719 g (17.521 mM) of tert-butyl 4-(ethoxycarbonylmethyl)-3,6-dihydro-2H-pyridine-1-carboxylate in 50 ml of tetrahydrofuran dropwise under ice-cooling and the mixture was stirred at room temperature for 1 hour. To this reaction mixture was added ethyl acetate with ice-cooling to decompose the excess lithium aluminum hydride. Then, water was added until a white precipitate had formed. The precipitate was filtered off with the aid of celite and the celite was washed with ethyl acetate. The filtrate and washes were pooled and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1) to provide the title compound.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customhad formed
  4. filtrationThe precipitate was filtered off with the aid of celite
  5. washthe celite was washed with ethyl acetate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1)

Sources & evidence

ORD record
ord-0ae7f7cf61bd4271b5970ff1bd6eaed8
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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