3-Methylpiperidine → HCID 86682904, compound

HRID 2368926Notes

Reaction equation

HRID 2368926 reaction equation
[C:1]([OH:10])(=[O:9])[C@@H:2]([C@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[CH3:11][CH:12]1[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]1>O>[C:6]([C@@H:4]([C@H:2]([C:1]([O-:10])=[O:9])[OH:3])[OH:5])([O-:8])=[O:7].[CH3:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][NH2+:14][CH2:13]1.[CH3:1][C@@H:2]1[CH2:4][CH2:6][CH2:15][NH2+:14][CH2:13]1

Participants

4

Reactant 2

HCID 790813-MethylpiperidineHCID 444305L-Tartaric acid

Product 1

HCID 86682904HCID 86682904, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of L-(+)-tartaric acid (37.9 g, 0.253 mol) in H2O (40 mL), racemic 3-methyl-piperidine (25 g, 0.252 mol) was added slowly. The mixture was kept at room temperature for 2 h. The desired isomer was crystallized from water and collected by filtration. The solid obtained was recrystallized three times from MeOH/EtOH/H2O=50/25/2 (154 mL) to give the desired product (13.5 g) as a white solid (99.6% ee). [Enantiomeric excess (% ee) was determined by HPLC after derivatization with Cbz-Val].

Workup

  1. customThe desired isomer was crystallized from water
  2. filtrationcollected by filtration
  3. customThe solid obtained
  4. customwas recrystallized three times from MeOH/EtOH/H2O=50/25/2 (154 mL)

Sources & evidence

ORD record
ord-572a8b16f419413788a7132cdd21e4f9
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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