Succinic anhydride → HCID 58482718, compound

HRID 1950745Notes

Reaction equation

HRID 1950745 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[C:18]1(=[O:24])[O:23][C:21](=[O:22])[CH2:20][CH2:19]1>CN(C1C=CN=CC=1)C.C(Cl)(Cl)Cl>[CH2:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][CH:2]([O:1][C:18]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:24])[CH2:7][CH2:6]1)=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 7922Succinic anhydrideHCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

Product 1

HCID 58482718HCID 58482718, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

Benzyl 4-hydroxy-1-piperidinecarboxylate (1.0 g, 4.25 mmol), succinic anhydride (0.425 g, 4.25 mmol) and 4-DMAP (52 mg, 0.425 mmol) were dissolved in CHCl3 (10 mL) and stirred for 24 hours. The volatiles were removed in vacuo. Aqueous NaHCO3 (100 mL) was added and the mixture was washed with Et2O (2×50 mL). The aqueous layer was acidified to pH=6 to 7 with 2N HCl and extracted with CH2Cl2 (2×60 mL). The combined organic extracts were washed with brine (60 mL), dried over Na2SO4 and concentrated in vacuo to afford compound 64 (768 mg, 54%) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 1.62 (m, 2H), 1.85 (m, 2H), 2.60-2.70 (m, 4H), 3.38 (m, 2H), 3.74 (m, 2H), 4.97 (m, 1H), 5.12 (s, 2H), 7.35 (m, 5H).

Workup

  1. customThe volatiles were removed in vacuo
  2. additionAqueous NaHCO3 (100 mL) was added
  3. washthe mixture was washed with Et2O (2×50 mL)
  4. extractionextracted with CH2Cl2 (2×60 mL)
  5. washThe combined organic extracts were washed with brine (60 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-28d27b733a5742f4819c47f9e710f4e8
Source dataset
uspto-grants-2013_03
Patent number
US08404664B2

Reaction notes

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