Nitromethane → Ethyl 4-hydroxy-4-(nitromethyl)-1-piperidinecarboxylate

HRID 1469227Notes

Reaction equation

HRID 1469227 reaction equation
[C:1]([N:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2].[O-]CC.[Na+].[N+:17]([CH3:20])([O-:19])=[O:18]>C(O)C>[OH:12][C:9]1([CH2:20][N+:17]([O-:19])=[O:18])[CH2:8][CH2:7][N:6]([C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 34767Ethyl 4-oxo-1-piperidinecarboxylateHCID 2723922Sodium ethoxide

Product 1

HCID 22708806Ethyl 4-hydroxy-4-(nitromethyl)-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of N-carbethoxy-4-piperidone (11.34 g, 66.24 mmol) in nitromethane (5.3 mL) and ethanol (2 mL) was added a solution of sodium ethoxide in ethanol (2.67 M, 1.24 mL, 3.31 mmol). The mixture was stirred for 5 min and a solution formed from which a solid precipitated. After 1.5 h, water (100 mL) was added and the solid was isolated by filtration, washed with water (100 mL), and dried under vacuum with heat to yield the product ethyl 4-hydroxy-4-(nitromethyl)piperidine-1-carboxylate as an off white solid, 9.58 g (62%).

Workup

  1. customa solution formed from which a solid
  2. customprecipitated
  3. waitAfter 1.5 h
  4. additionwater (100 mL) was added
  5. customthe solid was isolated by filtration
  6. washwashed with water (100 mL)
  7. customdried under vacuum
  8. temperaturewith heat

Sources & evidence

ORD record
ord-342b67800af64a4bbe1cc7f205609420
Source dataset
uspto-grants-2015_04
Patent number
US09006264B2

Reaction notes

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