Water → tert-Butyl (3S)-3-(hydroxymethyl)piperidine-1-carboxylate

HRID 1478602Notes

Reaction equation

HRID 1478602 reaction equation
C([C@:3]1([C:16]([O-])=[O:17])[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[OH:17][CH2:16][C@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 52194462HCID 52194462, compound

Product 1

HCID 1514448tert-Butyl (3S)-3-(hydroxymethyl)piperidine-1-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-1-tert-butyl 3-ethylpiperidine-1,3-dicarboxylate (4.27 g, 16.59 mmol) was dissolved in THF (100 ml), and then LiAlH4 (1.26 g, 33.19 mmol) was added at 0° C. The mixture was stirred for 1 hour, and then again at room temperature for 2 hours. When the reaction was completed, H2O (1.26 ml) was slowly added, and NaOH (15%, 1.26 ml) was slowly added. After that, H2O (4 ml) was added, followed by stirring at room temperature for 1 hour. The mixture was filtered through celite, and dried over MgSO4, followed by filtration and then concentration under reduced pressure, to give (S)-tert-butyl 3-(hydroxymethyl)piperidine-1-carboxylate (3.5 g, 99%).

Workup

  1. waitagain at room temperature for 2 hours
  2. stirringby stirring at room temperature for 1 hour
  3. filtrationThe mixture was filtered through celite
  4. dry with materialdried over MgSO4
  5. filtrationfollowed by filtration
  6. concentrationconcentration under reduced pressure

Sources & evidence

ORD record
ord-39eb6567300f41a7b92b47addf378aa5
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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