Hydrochloric Acid → (3S,6R)-1-((benzyloxy)carbonyl)-6-methylpiperidine-3-carboxylic acid

HRID 2367413Notes

Reaction equation

HRID 2367413 reaction equation
[CH3:1][C@H:2]1[N:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][C@@H:5]([C:18]([O:20]C)=[O:19])[CH2:4][CH2:3]1.O[Li].O.Cl>C1COCC1.O.CO>[CH3:1][C@H:2]1[N:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][C@@H:5]([C:18]([OH:20])=[O:19])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 51356004cis-1-Benzyl 3-methyl 6-methylpiperidine-1,3-dicarboxylate

Product 1

HCID 51357693(3S,6R)-1-((benzyloxy)carbonyl)-6-methylpiperidine-3-carboxylic acidYield 119%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of 3-methyl 1-(phenylmethyl) (3S,6R)-6-methyl-1,3-piperidinedicarboxylate (15 g, 51.5 mmol) in THF/water/CH3OH (10/5/1, 480 mL) was added LiOH.H2O (2.59 g, 61.8 mmol), and the reaction mixture was stirred at room temperature for about 1 hour. The mixture was acidified with 1N HCl until the pH was ˜5, and then concentrated in vacuo. The resulting residue was extracted with EtOAc (2×300 mL) and CHCl3 (2×300 mL), and the combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to afford the crude title compound (17 g). LC-MS (ES) m/z=278 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe resulting residue was extracted with EtOAc (2×300 mL) and CHCl3 (2×300 mL)
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1bc243804492428a97c5e30a39ecd3d3
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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