Diiodomethane → 1-tert-Butyl 4-ethyl 4-(iodomethyl)piperidine-1,4-dicarboxylate

HRID 278329Notes

Reaction equation

HRID 278329 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(NC(C)C)(C)C.[Li].[I:27][CH2:28]I>C1COCC1.CCCCCCC.C1COCC1.C(C1C=CC=CC=1)C.O>[I:27][CH2:28][C:6]1([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:8][CH2:7]1

Participants

7

Reactant 3

HCID 6346DiiodomethaneHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylateHCID 45051747Lithium diisopropylamine

Product 1

HCID 114180681-tert-Butyl 4-ethyl 4-(iodomethyl)piperidine-1,4-dicarboxylateYield 95.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 22742125Tetrahydrofuran heptane ethylbenzolSolvent

Procedure

To a solution of piperidine-1,4-dicarboxylic acid tert-butyl ester ethyl ester (12.8 g, 49.74 mmol) in 73 mL of dry THF under N2 atmosphere at −42° C. was added 24.87 mL (49.74 mmol) of 2M Lithium diisopropylamine in heptane/THF/ethylbenzene dropwise to not exceed −40° C. After one hour, 4.0 mL (49.74 mmol) of diiodomethane was added and the solution was warmed to ambient temperature overnight. The resulting solution was diluted with H2O and extracted with ethyl acetate. The organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide 18.84 g (95%) of the desired product as a brown oil. Electrospray Mass Spec: 398.2 (M+H)+

Workup

  1. customexceed −40° C
  2. extractionextracted with ethyl acetate
  3. washThe organics were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a4479234f781455e8ca737d2ca8094cc
Source dataset
uspto-grants-2002_03
Patent number
US06358980B1

Reaction notes

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