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Sodium Carbonate → (2R,5S)-Dimethyl 1-(2-(1,3-dioxoisoindolin-2-yl)ethyl)piperidine-2,5-dicarboxylate

HRID 1683317
Notes
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Reaction equation

HRID 1683317 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].O([CH2:15][CH2:16][N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])S(C(F)(F)F)(=O)=O.Cl.[CH3:29][O:30][C:31]([C@H:33]1[CH2:38][CH2:37][C@H:36]([C:39]([O:41][CH3:42])=[O:40])[CH2:35][NH:34]1)=[O:32]>O.C(Cl)Cl>[C:21]1(=[O:22])[N:17]([CH2:16][CH2:15][N:34]2[CH2:35][C@@H:36]([C:39]([O:41][CH3:42])=[O:40])[CH2:37][CH2:38][C@@H:33]2[C:31]([O:30][CH3:29])=[O:32])[C:18](=[O:27])[C:19]2=[CH:26][CH:25]=[CH:24][CH:23]=[C:20]12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 118094652-(1,3-Dioxoisoindolin-2-yl)ethyl trifluoromethanesulfonateHCID 67703709trans-2,5-Piperidine dicarboxylate dimethyl ester hydrochloride

Product 1

HCID 21782948(2R,5S)-Dimethyl 1-(2-(1,3-dioxoisoindolin-2-yl)ethyl)piperidine-2,5-dicarboxylateYield 99.1%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent2×

Procedure

To a well-stirred bi-phasic mixture consisting of sodium carbonate (500 g, 4.72 mol) in water (3 liters) and trans-2,5-piperidine dicarboxylate dimethyl ester hydrochloride (280 g, 1.18 mol in methylene chloride (4.5 liters), a solution of 2-phthalimido-ethyl triflate (417 g, 1.29 mol) in methylene chloride (3 liters) was added in a steady stream over a 3 hour period. The organic layer was separated, and the aqueous layer was extracted with fresh methylene chloride (3 liters). The combined organic extracts were washed with water (3 liters), then with brine (3 liters), dried with anhydrous magnesium sulfate and finally, concentrated in vacuo to a solid. The entire residue was triturated in resulting ether (3 liters), with vigorous stirring, for 15 minutes. After cooling to ambient temperature, the solution was poured into hexanes (3 liters), and the resulting mixture was stirred for 18 hours. The resulting colorless solid was collected by filtration, and the filter cake was washed with hexanes (1 liter). In vacuo drying afforded 437.3 g (99.1% yield) of the title compound as a colorless solid. TLC Rf (ethyl acetate/methylene chloride=1:1 in volume; iodoplatinate spray): 0.5.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with fresh methylene chloride (3 liters)
  3. washThe combined organic extracts were washed with water (3 liters)
  4. dry with materialwith brine (3 liters), dried with anhydrous magnesium sulfate
  5. concentrationfinally, concentrated in vacuo to a solid
  6. customThe entire residue was triturated
  7. customin resulting ether (3 liters)
  8. filtrationThe resulting colorless solid was collected by filtration
  9. washthe filter cake was washed with hexanes (1 liter)
  10. customIn vacuo drying

Sources & evidence

ORD record
ord-e3afcb94d2284800ab06f20d15406222
Source dataset
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05637713

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes