Trifluoroacetic acid → (3S)-3-Amino-4,4-dimethylpentan-2-one

HRID 2084547Notes

Reaction equation

HRID 2084547 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:13](=[O:15])[CH3:14])[C:9]([CH3:12])([CH3:11])[CH3:10])(C)(C)C.FC(F)(F)C(O)=O>ClCCl.CO>[NH2:7][C@@H:8]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:13](=[O:15])[CH3:14]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21305239(1(S)-Acetyl-2,2-dimethylpropyl)carbamic Acid-tert-butyl Ester

Product 1

HCID 21305288(3S)-3-Amino-4,4-dimethylpentan-2-oneYield 303.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1(S)-acetyl-2,2-dimethylpropyl)carbamic acid-tert-butyl ester (700 mg, 2.55 mmol) in dichloromethane (10 mL) at 0° C. was added trifluoroacetic acid (5 mL). The reaction was left at <5° C. for 16 hours before the solvents were removed in vacuo to give a bright yellow oil. The residue was dissolved in methanol (30 mL) and was treated portionwise with Dowex 1X8-400 basic resin until pH 9. Filtration and removal of the solvents in vacuo gave the title compound as a pale yellow oil (˜1.0 g, >100%, residual water). The material was used without further purification.

Workup

  1. customwere removed in vacuo
  2. customto give a bright yellow oil
  3. additionwas treated portionwise with Dowex 1X8-400 basic resin until pH 9
  4. filtrationFiltration and removal of the solvents in vacuo

Sources & evidence

ORD record
ord-872bafbceae144b49a8f6de31ccf3ac3
Source dataset
uspto-grants-2004_04
Patent number
US06716878B1

Reaction notes

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