Acetic Acid → Tert-butyl 3-cyano-3-hydroxypiperidine-1-carboxylate

HRID 705690Notes

Reaction equation

HRID 705690 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C-:15]#[N:16].[K+].C(O)(=O)C>C1COCC1.O>[C:15]([C:10]1([OH:14])[CH2:11][CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1)#[N:16]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylate

Product 1

HCID 58487593Tert-butyl 3-cyano-3-hydroxypiperidine-1-carboxylateYield 96.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-Boc-3-piperidinone (5.0 g, 0.0251 mol) in THF (15 mL) was added dropwise to a solution of potassium cyanide (1.8 g 0.0276 mol) in water (15 mL) at 0-5° C. Acetic acid (1.6 mL, 0.0276 mol) was added and the solution was allowed to warm to room temperature and stir for 1 hr. The mixture was partitioned between water (50 mL) and ethyl acetate (1×150 mL). The organics were washed with 2×50 mL water, 1×50 mL saturated sodium chloride, and dried over Na2SO4. The dried organics were evaporated to obtain 5.5 g of yellow solid. The material was used without purification. MS (ESI) m/z 265 [M+K]+.

Workup

  1. customThe mixture was partitioned between water (50 mL) and ethyl acetate (1×150 mL)
  2. washThe organics were washed with 2×50 mL water, 1×50 mL saturated sodium chloride
  3. dry with materialdried over Na2SO4
  4. customThe dried organics were evaporated

Sources & evidence

ORD record
ord-aa493d50194947a4938b5f0e556889dc
Source dataset
uspto-grants-2015_11
Patent number
US09174972B2

Reaction notes

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