Malononitrile → HCID 58116980, compound

HRID 38538Notes

Reaction equation

HRID 38538 reaction equation
[OH:1][CH:2]1[C:7](=O)[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.[C:16](#[N:20])[CH2:17][C:18]#[N:19].C(NCC)C>C(O)C>[NH2:20][C:16]1[O:1][C:2]2[CH2:3][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:6][C:7]=2[C:17]=1[C:18]#[N:19]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8021DiethylamineHCID 58116959tert-Butyl 3-hydroxy-4-oxopiperidine-1-carboxylate

Product 1

HCID 58116980HCID 58116980, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl 3-hydroxy-4-oxopiperidine-1-carboxylate from Example 45A (3.88 g, 64% purity, 11.5 mmol) was dissolved in ethanol (10 mL), and propanedinitrile (758 mg, 11.5 mmol) was added. Within 10 min, diethylamine (0.84 g, 11.5 mmol) was added dropwise, whilst the temperature was kept below 30° C. Subsequently, the reaction mixture was stirred for 20 h at rt. The solvent was removed in vacuo, and the residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1). The product was triturated with petroleum ether/tert-butyl methyl ether (3:1) to yield 1.45 g (47%) of the title compound as yellow crystals.

Workup

  1. customwas kept below 30° C
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1)
  4. customThe product was triturated with petroleum ether/tert-butyl methyl ether (3:1)

Sources & evidence

ORD record
ord-67dcab49e44541928515fa48a0dd6726
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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