Methyl iodide → Tert-butyl 3-(3-chlorophenyl)-2-methyl-3-oxopropyl(methyl)carbamate

HRID 426045Notes

Reaction equation

HRID 426045 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:10](=[O:22])[CH2:11][CH2:12][N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:7]=[CH:8][CH:9]=1.[CH3:23]I>C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([C:10](=[O:22])[CH:11]([CH3:23])[CH2:12][N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59364354Tert-butyl 3-(3-chlorophenyl)-3-oxopropyl(methyl)carbamate

Product 1

HCID 66704415Tert-butyl 3-(3-chlorophenyl)-2-methyl-3-oxopropyl(methyl)carbamateYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To NaH (680 mg, 1.7 mmol) in THF (10 mL) was added tert-butyl 3-(3-chlorophenyl)-3-oxopropyl(methyl)carbamate (2.4 g, 8.5 mmol) in THF (5 mL) at 0° C. over 3 min. After a few minutes THF (100 mL) was added. And an additional 10 min, CH3I (1.32 g, 9.3 mmol) was added drop wise. The mixture was stirred for 16 h at room temperature. Then the mixture was quenched with NH4Cl and 1N HCl was added until pH=4 was reached. The mixture was extracted with ethyl acetate. The organic layers was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by chromatography to give the product (2.0 g, 79%).

Workup

  1. customThen the mixture was quenched with NH4Cl and 1N HCl
  2. additionwas added until pH=4
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layers was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-d22dd507a56d43e283d8522161f49281
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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