Succinic anhydride → HCID 66942044, compound

HRID 2106502Notes

Reaction equation

HRID 2106502 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[C:4]([CH2:3][CH2:2][C:1]([N:24]1[CH2:23][CH2:22][CH:21]([CH:18]2[CH2:17][CH2:16][N:15]([C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:14])[CH2:20][CH2:19]2)[CH2:26][CH2:25]1)=[O:7])([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 7922Succinic anhydride2×HCID 11430Potassium CarbonateHCID 117475994,4'-Bipiperidine, 1-boc protected

Product 1

HCID 66942044HCID 66942044, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4.1 g (40.7 mmol) succinic acid anhydride in 50 mL THF was added dropwise at RT to a solution of 10.0 g (37.3 mmol) tert-butyl[4,4′]bipiperidinyl-1-carboxylate in 100 mL THF and the reaction mixture was stirred overnight at RT. To complete the reaction another 2.0 g (19.9 mmol) succinic acid anhydride were added, the mixture was stirred for 4 h at 50° C. and stirred overnight at RT. 200 mL of 7.5% K2CO3 solution was added and the aqueous phase was washed with 200 mL EtOAc. The organic phase was extracted with 200 mL 7.5% K2CO3 solution and the combined aqueous phases were acidified with citric acid. The mixture was extracted exhaustively with EtOAc and the combined organic phases were evaporated down i. vac.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred for 4 h at 50° C.
  3. stirringstirred overnight at RT
  4. washthe aqueous phase was washed with 200 mL EtOAc
  5. extractionThe organic phase was extracted with 200 mL 7.5% K2CO3 solution
  6. extractionThe mixture was extracted exhaustively with EtOAc
  7. customthe combined organic phases were evaporated down i

Sources & evidence

ORD record
ord-3c089e17b22645debf6b380c9fef6183
Source dataset
uspto-grants-2009_08
Patent number
US07579341B2

Reaction notes

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