Sodium Cyanide → tert-Butyl 4-cyano-4-hydroxypiperidine-1-carboxylate

HRID 733108Notes

Reaction equation

HRID 733108 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[C-:15]#[N:16].[Na+].C([O-])(O)=O.[Na+]>C(OCC)C.O>[C:15]([C:2]1([OH:1])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1)#[N:16]

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 53399262tert-Butyl 4-cyano-4-hydroxypiperidine-1-carboxylateYield 92.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of tert-butyl 4-oxopiperidine-1-carboxylate (2.0 g, 10 mmol) in diethyl ether (40 mL), a solution of NaCN (0.54 g, 11 mmol) and NaHCO3 (1.7 g, 20 mmol) in water (25 mL) was added slowly with vigorous stirring at room temperature. The mixture was stirred overnight, and extracted with Et2O (30 mL×2). The organic phase was washed with water (50 mL), brine (50 mL) and dried over MgSO4, filtered and evaporated gave 2.1 g of the title compound as clear colorless oil.

Workup

  1. stirringThe mixture was stirred overnight
  2. extractionextracted with Et2O (30 mL×2)
  3. washThe organic phase was washed with water (50 mL), brine (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ee8db33dc297408fb37a562a63ca671a
Source dataset
uspto-grants-2009_09
Patent number
US07589109B2

Reaction notes

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