Potassium Hydroxide → 1-Boc-1,2,5,6-tetrahydropyridine-3-carboxylic acid

HRID 1003382Notes

Reaction equation

HRID 1003382 reaction equation
[OH-].[K+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]=[C:12]([C:16]([O:18]C)=[O:17])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>O.CO>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]=[C:12]([C:16]([OH:18])=[O:17])[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 111284441-Tert-butyl 3-methyl 1,2,5,6-tetrahydropyridine-1,3-dicarboxylate

Product 1

HCID 130325691-Boc-1,2,5,6-tetrahydropyridine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (44 g, 0.79 mol) in water (450 ml) was added to a solution of methyl 1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate (34.9 g, 145 mmol) in methanol (450 ml). The mixture was refluxed for 3h and evaporated to dryness in vacuo. The residue acidified to pH 2.5 with hydrochloric acid (4M) and extracted with methylene chloride. The organic layer was dried over magnesium sulphate and evaporated to dryness in vacuo to give 1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid. (Yield: 28.4g, 86%)

Workup

  1. customevaporated to dryness in vacuo
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-033ea94701f3487091e5dc28625cac77
Source dataset
uspto-grants-2000_04
Patent number
US06046214

Reaction notes

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