tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate → tert-butyl N-(2-cyclohexyl-2-oxoethyl)carbamate

HRID 254834Notes

Reaction equation

HRID 254834 reaction equation
CON(C)[C:4](=[O:14])[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[CH:16]1([Mg]Cl)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C1COCC1>[CH:16]1([C:4](=[O:14])[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 4428209tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamateHCID 178478990HCID 178478990, compound

Product 1

HCID 58430272tert-butyl N-(2-cyclohexyl-2-oxoethyl)carbamateYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tert-butyl 2-(methoxy(methyl)amino)-2-oxoethylcarbamate (400 mg, 1.83 mmol) in THF (10 mL) was added cyclohexylmagnesium chloride (4.12 mL, 8.24 mmol) portionwise at room temperature under N2 atmosphere. As addition of the Grignard reagent was completed, the reaction mixture was stirred and heated to reflux for an hour. Then the mixture was allowed to cool down to room temperature. The reaction was quenched by adding water (10 mL) slowly. 1N HCl solution (30 mL) was added to the mixture, and extracted with EtOAc (20 mL×3). The combined organic layers were collected and evaporated in vacuo. The crude material was purified by column chromatography (hexane: EtOAc=10:1 to 5:1) to yield the desired product (110 mg, 25%).

Workup

  1. temperatureheated
  2. temperatureto reflux for an hour
  3. customThe reaction was quenched
  4. additionby adding water (10 mL) slowly
  5. addition1N HCl solution (30 mL) was added to the mixture
  6. extractionextracted with EtOAc (20 mL×3)
  7. customThe combined organic layers were collected
  8. customevaporated in vacuo
  9. customThe crude material was purified by column chromatography (hexane: EtOAc=10:1 to 5:1)

Sources & evidence

ORD record
ord-20754f005eac4534a5e7cbe8c83c05ff
Source dataset
uspto-grants-2011_01
Patent number
US07875647B2

Reaction notes

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