Methanol → methyl piperidine-1-carboxylate

HRID 1019355

Reaction equation

HRID 1019355 reaction equation
[N:1]1([C:7]([O:9][CH2:10]C)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CO.C[O-].[Na+]>C1COCC1>[N:1]1([C:7]([O:9][CH3:10])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 213991-Piperidinecarboxylic acid, ethyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 232666methyl piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Polymer-bound piperidinecarboxylic acid, ethyl ester resin (0.25 g, 0.283 mmol) was swollen with a solution of MeOH (1 ml) in THF (4 ml) in a QUICKFIT test-tube. After addition of sodium methoxide (0.28 ml, 0.028 mmol, 1M solution in MeOH) the resulting suspension was stirred overnight at reflux. The reaction suspension was cooled down to room temperature and the resin was washed using VACMASTER station with DCM (4×3 ml), MeOH (2×3 ml) and then dried under vacuum. FT-IR (2% w/w KBr disk): C=0 1736 cm−1 (ester); 163 cm−1 (amide).

Workup

  1. temperatureat reflux
  2. washthe resin was washed
  3. customdried under vacuum

Sources & evidence

ORD record
ord-4b3d8bc8afbd4dad84dbdd0dff1214b2
Source dataset
uspto-grants-2002_11
Patent number
US06486354B1

Linked notes

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