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

HRID 1193332Notes

Reaction equation

HRID 1193332 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. A colourless oil was obtained, which was used in the next stage without being purified 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 further

Sources & evidence

ORD record
ord-28b820a6546847a38d6f9aa925521a3a
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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