Methanol → HCID 66731865, compound

HRID 1963300Notes

Reaction equation

HRID 1963300 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][CH:7]2[CH2:12][CH:11]([C:13]([O:15]C)=[O:14])[CH2:10][CH2:9][N:8]2[C:17]([O:19][CH3:20])=[O:18])=[CH:4][CH:3]=1.[Li+].[OH-].CO.O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:12][CH:11]([C:13]([OH:15])=[O:14])[CH2:10][CH2:9][N:8]2[C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962Water2×HCID 3939Lithium HydroxideHCID 66734600HCID 66734600, compound

Product 1

HCID 66731865HCID 66731865, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dimethyl 2-(4-chlorobenzyl)piperidine-1,4-dicarboxylate (4.74 g, 14.55 mmol) was dissolved in tetrahydrofuran (15 mL) followed by addition of LiOH (0.430 g, 17.97 mmol), MeOH (10 mL) and water (10 mL). The reaction mixture was stirred at room temperature overnight. The solvents were evaporated and the residue was taken up in water. The pH was adjusted to <2 by addition of 2 M HCl. The product was poorly soluble and attempts to extract the aqueous phase with DCM and ethyl acetate failed. Instead the mixture was concentrated and then filtered, washed with water and dried to give a yellow solid material. The water phase did contain some product and was extracted with DCM (×3) and dried with a phase separator to give about 500 mg. Crude 2-(4-chlorobenzyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (4.27 g, quant.) was isolated. MS m/z 312, 314 (M+H)+

Workup

  1. customThe solvents were evaporated
  2. additionThe pH was adjusted to <2 by addition of 2 M HCl
  3. extractionto extract the aqueous phase with DCM and ethyl acetate
  4. concentrationInstead the mixture was concentrated
  5. filtrationfiltered
  6. washwashed with water
  7. customdried
  8. customto give a yellow solid material
  9. extractionwas extracted with DCM (×3)
  10. customdried with a phase separator
  11. customto give about 500 mg

Sources & evidence

ORD record
ord-e2fab0f8379c4c078830ec1bbd1c80a6
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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