Methyl iodide → HCID 178496620, compound

HRID 1506249Notes

Reaction equation

HRID 1506249 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.[H-].[Na+].[CH2:18]1OCCOCCOCCOCCOC1.IC>O1CCCC1.CO>[CH3:18][O:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 178418329HCID 178418329, compound

Product 1

HCID 178496620HCID 178496620, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl (trans-4-hydroxycyclohexyl)carbamate (1.0 g, 4.6 mmol) in tetrahydrofuran (20 mL) was stirred with sodium hydride (55 wt % dispersion in mineral oil, 24 mg, 6.4 mmol) and 15-crown-5 ether (965 μL) for 30 minutes under cooling with ice and then with iodomethane (289 μL) at room temperature for 1 hour. Methanol (2 mL) was added to the reaction mixture, and the precipitated solid was removed by filtration. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=8/1 (v/v)) to give the title compound (708 mg, yield 67%).

Workup

  1. temperatureunder cooling with ice
  2. customthe precipitated solid was removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=8/1 (v/v))

Sources & evidence

ORD record
ord-6b73546813a8493596edb49f86fb9440
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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