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

HRID 1837894Notes

Reaction equation

HRID 1837894 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 11-3 (10.0 g, 40.5 mmol) and THF (200 ml) at 0° C. was added methylmagnesium bromide (27.0 ml, 91.0 mmol; 3M in ether) dropwise over 20 minutes. After 2.0 hours, 10% KHSO4 was added slowly. The mixture was extracted with EtOAc. The organic portion was washed with sat. NaHCO3, brine, and dried over MgSO4. Evaporative removal of the solvent gave 11-4 as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-da0b698e4b5146039f705a9d2f9fe000
Source dataset
uspto-grants-2004_08
Patent number
US06784190B2

Reaction notes

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