1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Succinimido 1-t-butoxycarbonylpiperidine-4-carboxylate

HRID 2288728Notes

Reaction equation

HRID 2288728 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([C:22](O)=[O:23])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].CCN=C=NCCCN(C)C>CN(C=O)C>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([C:22]([O:1][N:2]2[C:6](=[O:7])[CH2:5][CH2:4][C:3]2=[O:8])=[O:23])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2×HCID 80170N-HydroxysuccinimideHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 15578030Succinimido 1-t-butoxycarbonylpiperidine-4-carboxylateYield 84.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

N-Hydroxysuccinimide (25.3 g) was added to a solution of 1-(t-butoxycarbonyl)piperidine-4-carboxylic acid (45.8 g) in DMF (250 ml) and the mixture stirred at 5° C. EDAC (42 g) was added and the mixture stirred for 4 hours at 5° C. A further portion of EDAC (5.73 g) was added and the mixture allowed to warm to ambient temperature and stirred overnight. The mixture was evaporated to half its original volume and the residue partitioned between ethyl acetate (1000 ml) and water (250 ml). The ethyl acetate phase was separated, washed with water (2×250 ml), brine (50 ml), dried (MgSO4) and evaporated to give a solid which was recrystallised from a mixture of ethyl acetate/hexane (250 ml/500 ml) to give 1-(1-(t-butoxycarbonyl)piperidin-4-ylcarbonyloxy)2,5-dioxopyrrolidine (55 g);

Workup

  1. stirringthe mixture stirred for 4 hours at 5° C
  2. temperatureto warm to ambient temperature
  3. stirringstirred overnight
  4. customThe mixture was evaporated to half its original volume
  5. customthe residue partitioned between ethyl acetate (1000 ml) and water (250 ml)
  6. customThe ethyl acetate phase was separated
  7. washwashed with water (2×250 ml), brine (50 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto give a solid which
  11. customwas recrystallised from a mixture of ethyl acetate/hexane (250 ml/500 ml)

Sources & evidence

ORD record
ord-519f144105e14950af2bd32110c8b480
Source dataset
uspto-grants-2000_07
Patent number
US06090813

Reaction notes

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