Isopropyl iodide → HCID 68313045, compound

HRID 1530571Notes

Reaction equation

HRID 1530571 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 mixture 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 portion. 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 eluting with a 5-10% gradient of MeOH in DCM to afford tert-butyl 2-(1-isopropylpiperidin-4-yl)pyrrolidine-1-carboxylate (302 mg, 65% yield). A solution of tert-butyl 2-(1-isopropylpiperidin-4-yl)pyrrolidine-1-carboxylate (302 mg, 1.02 mmol) in sat. HCl/dioxane (5 mL) was stirred at room temperature for 8 h. After removal of the solvent, 1-isopropyl-4-(pyrrolidin-2-yl)piperidine hydrochloride (232 mg, 100% yield) as yellow solid was obtained. LCMS (ESI) m/z: 197.2 [M+H+].

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
  6. washeluting with a 5-10% gradient of MeOH in DCM

Sources & evidence

ORD record
ord-cb9680b24a0241b6b11a4d85fea7613a
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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