Benzyl chloroformate → rac-(2R,3S)-1-[(benzyloxy)carbonyl]-3-methylpiperidine-2-carboxylic acid

HRID 590951Notes

Reaction equation

HRID 590951 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][NH:4][C@H:3]1[C:8]([OH:10])=[O:9].[OH-].[Na+].[C:13](Cl)([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>O1CCOCC1>[CH2:16]([O:15][C:13]([N:4]1[CH2:5][CH2:6][CH2:7][C@H:2]([CH3:1])[C@@H:3]1[C:8]([OH:10])=[O:9])=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 40153962(2R,3S)-3-Methylpiperidine-2-carboxylic acid

Product 1

HCID 66624874rac-(2R,3S)-1-[(benzyloxy)carbonyl]-3-methylpiperidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(+/−)-Cis-3-methylpiperidine-2-carboxylic acid (10.4 g, 72.9 mmol) in 1,4-dioxane (200 mL) and 1 N NaOH (218 mL, 219 mmol) was treated with CBzCl (15.4 mL, 109 mmol) and stirred for 18 h. The mixture concentrated and the resulting solid was suspended in EtOAc (200 mL) and the mixture was filtered. The solids were washed with EtOAc (3 50 mL) and the solution was dried over MgSO4. The solution was concentrated to afford (+/−)-cis-1-(benzyloxycarbonyl)-3-methylpiperidine-2-carboxylic acid, which was used without further purification.

Workup

  1. concentrationThe mixture concentrated
  2. filtrationthe mixture was filtered
  3. washThe solids were washed with EtOAc (3 50 mL)
  4. dry with materialthe solution was dried over MgSO4
  5. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-6f37884822a049538baeaf7e8f87c339
Source dataset
uspto-grants-2016_01
Patent number
US09238039B2

Reaction notes

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