Methyl iodide → HCID 118133429, compound

HRID 1050575Notes

Reaction equation

HRID 1050575 reaction equation
[CH3:1][C@@H:2]1[C@H:7]([N:8]2[CH2:12][CH2:11][NH:10][C:9]2=[O:13])[CH2:6][CH2:5][CH2:4][N:3]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].[H-].[Na+].I[CH3:27]>C1COCC1.CCOC(C)=O.O>[CH3:1][C@@H:2]1[C@H:7]([N:8]2[CH2:12][CH2:11][N:10]([CH3:27])[C:9]2=[O:13])[CH2:6][CH2:5][CH2:4][N:3]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 118133431HCID 118133431, compound

Product 1

HCID 118133429HCID 118133429, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 354 (490 mg, 1.55 mmol) was dissolved in 15 mL dry THF. It was treated with NaH (60% in mineral oil, 125 mg, 3.1 mmol) for 15 min at RT. To the mixture was then added iodomethane (200 μL, 3.1 mmol). The mixture was stirred at RT for 1.5 hour, diluted with 150 mL EtOAc and 50 water. The organic phase was separated, washed with water, dried, concentrated, and subjected to silica flash column using 0 to 4% MeOH in DCM to isolate (2R,3R)-benzyl 2-methyl-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidine-1-carboxylate (355, 470 mg, 92%). It was dissolved in 100 mL iPrOH. To it was added 10% Pd/C (0.5 g), and the mixture was hydrogenated at 40 psi on a Parr shaker for overnight. The mixture was filtered through celite and concentrated in vacuo to give 1-methyl-3-((2R,3R)-2-methylpiperidin-3-yl)imidazolidin-2-one (356) as a white solid in quantitative yield.

Workup

  1. customThe organic phase was separated
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b72453bce6f64c1c84fe8fd2a230749f
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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