Sodium Carbonate → 1-(Phenylmethyl) (3R)-1,3-piperidinedicarboxylate

HRID 1969714Notes

Reaction equation

HRID 1969714 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([C:7]([OH:9])=[O:8])[CH2:2]1.[C:10](=O)([O:19]N1C(=O)CCC1=O)[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>O>[CH2:12]([O:11][C:10]([N:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([C:7]([OH:9])=[O:8])[CH2:2]1)=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 83172Benzyl succinimido carbonateHCID 1796510(-)-Nipecotic acid

Product 1

HCID 7365381-(Phenylmethyl) (3R)-1,3-piperidinedicarboxylateYield 191.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (R)-piperidine-3-carboxylic acid (3.0 g, 23 mmol), benzyl 2,5-dioxopyrrolidin-1-yl carbonate (5.79 g, 23.2 mmol) and Na2CO3 (6.15 g, 58.1 mmol) was stirred in water and 1,4-dioxane (1:1, 200 mL) at ambient temperature for about 96 h. The organic solvent was removed under reduced pressure. The aqueous layer was acidified with 1 N aqueous HCl and extracted with EtOAc (2×100 mL). The organic phase was washed with brine (150 mL), dried over anhydrous MgSO4 and concd under reduced pressure to yield crude (R)-1-(benzyloxycarbonyl)-piperidine-3-carboxylic acid (11.6 g, 191%) as a white solid: LC/MS (Table 1, Method a) Rt=1.80 min; MS m/z 264 (M+H)+.

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe organic phase was washed with brine (150 mL)
  4. dry with materialdried over anhydrous MgSO4 and concd under reduced pressure

Sources & evidence

ORD record
ord-b94f5f9d6974462baba83a8274bc240b
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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