Sodium borohydride → tert-Butyl 4-(3-hydroxybutyl)piperidine-1-carboxylate

HRID 2368080Notes

Reaction equation

HRID 2368080 reaction equation
[O:1]=[C:2]([CH3:18])[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.[BH4-].[Na+]>C(O)C>[OH:1][CH:2]([CH3:18])[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 575174821196894-98-0

Product 1

HCID 57517483tert-Butyl 4-(3-hydroxybutyl)piperidine-1-carboxylateYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 4-(3-oxobutyl)piperidine-1-carboxylate (3.7 g) in ethanol (40 mL) was added sodium borohydride (550 mg) at room temperature, and the mixture was stirred at room temperature for 30 min. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate and water. The organic layer was separated, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (3.71 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-46f736bc081045c9b01ac205f82d435e
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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