Sodium Sulfate → 1-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

HRID 1193296Notes

Reaction equation

HRID 1193296 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[OH:9][CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 9993342Ethyl 1-((1,1-dimethylethoxy)carbonyl)-4-piperidineacetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidineYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LAH (819 mg, 21.58 mmol, 1.3 eq) was placed in THF (50 ml) at 0° C.; a solution of tert-butyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate (4.5 g, 16.60 mmol, 1 eq) in THF (50 ml) was added dropwise and then stirring was carried out for 1 h at RT. After monitoring by thin-layer chromatography, the reaction mixture was hydrolyzed with sat. sodium sulfate solution (2 ml), filtered over Celite and washed with THF (300 ml). The filtrate was concentrated under reduced pressure and a colourless oil was obtained, which was used in the next stage without being purified and analyzed further. Yield: 92% (3.5 g, 15.28 mmol).

Workup

  1. filtrationfiltered over Celite
  2. washwashed with THF (300 ml)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customa colourless oil was obtained
  5. customwithout being purified

Sources & evidence

ORD record
ord-f2810d83493a431b81927fdf0389a54c
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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