Methyl iodide → HCID 178496620, compound

HRID 2111585Notes

Reaction equation

HRID 2111585 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:18]1OCCOCCOCCOCCOC1.IC>C1COCC1>[C:3]([O:7][C:8]([NH:10][C@H:11]1[CH2:12][CH2:13][C@H:14]([O:17][CH3:18])[CH2:15][CH2:16]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

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

Product 1

HCID 178496620HCID 178496620, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% in mineral oil, 278 mg, 6.96 mmol) was suspended in THF (5 mL) and cooled to 0° C. trans-tert-Butoxy-N-(4-hydroxycyclohexyl) carboxamide (1 g, 4.64 mmol) and 15-crown-5 (0.965 mL, 4.88 mmol) were added and the reaction mixture was stirred at 0° C. for about 30 minutes. Iodomethane (0.289 mL, 4.64 mmol) was added and the reaction stirred at 0° C. for about 1 hour after which the LCMS showed it was complete. The reaction was quenched with methanol, the solvents removed in vacuo and the crude purified by column chromatography (SiO2, 8:2 n-hexanes/ethyl acetate) to afford 642 mg of the methyl ether. ES-MS: 230 (M+1).

Workup

  1. additionwere added
  2. stirringthe reaction stirred at 0° C. for about 1 hour after which the LCMS
  3. customThe reaction was quenched with methanol
  4. customthe solvents removed in vacuo
  5. customthe crude purified by column chromatography (SiO2, 8:2 n-hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-d7c3fd480c6c459ea92d46bd68188e9a
Source dataset
uspto-grants-2009_04
Patent number
US07521446B2

Reaction notes

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