Lithium Hydroxide → 1-[(Benzyloxy)carbonyl]-3-methylpiperidine-3-carboxylic acid

HRID 2203795Notes

Reaction equation

HRID 2203795 reaction equation
[Li+].[OH-].[CH3:3][C:4]1([C:20]([O:22]CC)=[O:21])[CH2:9][CH2:8][CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5]1>C(O)C>[CH2:13]([O:12][C:10]([N:6]1[CH2:7][CH2:8][CH2:9][C:4]([CH3:3])([C:20]([OH:22])=[O:21])[CH2:5]1)=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 534862661-Benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate

Product 1

HCID 532493621-[(Benzyloxy)carbonyl]-3-methylpiperidine-3-carboxylic acidYield 93.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
86 °C

Procedure

LiOH (15.0 mL, 30.1 mmol) was added to 1-benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate (3.0 g, 10.0 mmol) in ethanol (15 mL), and the reaction mixture was stirred at 86° C. for 1 hour. The ethanol was removed, and ether (30 mL) was added. The aqueous layer was separated and acidified with saturated potassium hydrogen sulfate to a pH of about 3 to about 4, extracted with ethyl acetate (50 mL), washed with brine and dried over sodium sulfate. After removal of the solvent, 1-(benzyloxycarbonyl)-3-methylpiperidine-3-carboxylic acid (2.6 g, 92% yield) was isolated as an oil.

Workup

  1. customThe ethanol was removed
  2. additionether (30 mL) was added
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (50 mL)
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customAfter removal of the solvent

Sources & evidence

ORD record
ord-08206959d63a4f108010fec6924b1626
Source dataset
uspto-grants-2016_06
Patent number
US09365568B2

Reaction notes

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