Lithium Hydroxide → HCID 59546398, compound

HRID 1691586Notes

Reaction equation

HRID 1691586 reaction equation
[CH2:1]([N:3]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:4]([N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]1[C:12]([O:14]C)=[O:13])=[O:5])[CH3:2].[Li+].[OH-]>CO>[CH2:1]([N:3]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:4]([N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]1[C:12]([OH:14])=[O:13])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59546408HCID 59546408, compound

Product 1

HCID 59546398HCID 59546398, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To (S)-methyl 1-(N-ethyl-N-phenylcarbamoyl)piperidine-2-carboxylate (0.15 g, 0.5 mmol) dissolved in methanol (2.0 mL) was added a solution of LiOH (1.0 N, 8.0 equiv). The reaction was heated to 50° C. and stirred at this temperature for 4 h. The solvent was then removed and pH was adjusted to 4 by addition of 1N HCl. The mixture was extracted with dichloromethane and evaporation of the solvent afforded (S)-1-(N-ethyl-N-phenylcarbamoyl)piperidine-2-carboxylic acid (0.1 g, 72% yield). 1H NMR (500 MHz, CD2Cl2) δ 1.00-1.10 (m, 4H), 1.40-1.55 (m, 3H), 2.10 (m, 2H), 2.5 (m, 1H), 3.2 (d, 1H), 3.50-3.55 (m, 2H), 3.65-3.70 (m, 1H), 4.4 (t, 1H), 7.10-7.25 (m, 3H), 7.30-7.45 (m, 2H), 12.5 (br s, 1H).

Workup

  1. customThe solvent was then removed
  2. additionpH was adjusted to 4 by addition of 1N HCl
  3. extractionThe mixture was extracted with dichloromethane and evaporation of the solvent

Sources & evidence

ORD record
ord-cdb83f1979874b4398320311a76e3b00
Source dataset
uspto-grants-2012_04
Patent number
US08153785B2

Reaction notes

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