Potassium bisulfate → tert-Butyl (4-oxopentyl)carbamate

HRID 2289158Notes

Reaction equation

HRID 2289158 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][CH2:10][C:11](=[O:16])N(OC)C)([CH3:4])([CH3:3])[CH3:2].[CH3:18][Mg]Br.OS([O-])(=O)=O.[K+]>C1COCC1>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][CH2:10][C:11](=[O:16])[CH3:18])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 23112516tert-butyl N-(3-(methoxy(methyl)carbamoyl)propyl)carbamateHCID 178418573HCID 178418573, compound

Product 1

HCID 21478928tert-Butyl (4-oxopentyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-3 (10.0 g, 40.5 mmol) and THF (200 ml) at 0° C. was added methyl magnesium bromide (27.0 ml, 91.0 mmol; 3M in ether) dropwise over 20 minutes. Mter 2.0 hours, 10% KHSO4 was added slowly. The mixture was extracted with EtOAc. The organic portion was washed with saturated NaHCO3, brine, and dried over MgSO4. Evaporative removal of the solvent gave 1-4 as a colorless oil.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washThe organic portion was washed with saturated NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. customEvaporative removal of the solvent

Sources & evidence

ORD record
ord-696f3cf5a37a4ce09e24f18fba1559ba
Source dataset
uspto-grants-2000_07
Patent number
US06090944

Reaction notes

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