Isopropyl iodide → HCID 68313045, compound

HRID 1530661Notes

Reaction equation

HRID 1530661 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3][CH2:2]1.[H-].[Na+].I[CH:22]([CH3:24])[CH3:23]>CN(C=O)C>[CH:22]([N:1]1[CH2:2][CH2:3][CH:4]([CH:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:5][CH2:6]1)([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 162288381,1-Dimethylethyl 2-(4-piperidinyl)-1-pyrrolidinecarboxylate

Product 1

HCID 68313045HCID 68313045, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 2-(piperidin-4-yl)pyrrolidine-1-carboxylate (400 mg, 1.57 mmol) in dry DMF (2.0 mL) at 0° C., was added NaH (132 mg, 3.30 mmol, 60% in mineral oil) in small portions. The reaction mixture was then warmed to room temperature with stirring for another 1 h. 2-iodopropane (2.0 mL) was added. The resulting mixture was stirred at room temperature for 24 h and then poured into the ice-water (20 mL). The resultant mixture was extracted with EtOAc (2×50 mL). The combined organic layers were dried over Na2SO4 and evaporated to dryness. The residue was purified by silica gel chromatography using 5-10% MeOH in DCM as eluant to afford the desired product (302 mg, 65% yield). LCMS m/z [M+H]+ 297.2.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 24 h
  2. extractionThe resultant mixture was extracted with EtOAc (2×50 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customevaporated to dryness
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3aae703866994a208061271977b68e26
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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