Triethylamine → HCID 17819432, compound

HRID 963453Notes

Reaction equation

HRID 963453 reaction equation
[CH2:1]([O:5][C:6]([NH:8][CH:9]([C:12]([F:15])([CH3:14])[CH3:13])[CH2:10]I)=[O:7])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C>C(O)C.[OH-].[Pd+2].[OH-]>[CH2:1]([O:5][C:6]([NH:8][CH:9]([C:12]([F:15])([CH3:13])[CH3:14])[CH3:10])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 17819417HCID 17819417, compound

Product 1

HCID 17819432HCID 17819432, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A Parr bottle was charged with palladium (II) hydroxide (800 mg), a solution of N-butoxycarbonyl-1-iodo-2-amino-3-fluoro-3-methyl-n-butane (3.26 g, 9.8 mmol) in ethanol (80 mL) and triethylamine (0.99 g, 9.8 mmol). The reaction mixture was placed under hydrogen gas (50 psig) and shaken for 20 hours. The mixture was filtered through celite and evaporated. The residue was dissolved in diethyl ether (100 mL) and washed with 1N aq. HCl (2×50 mL), water (2×50 mL), and then dried (MgSO4). Filtration and evaporation gave a residue that was chromatographed (silica gel, diethyl ether/hexane (3/1)) to afford 1.80 g of N-butoxycarbonyl-2-amino-3-fluoro-3-methyl-n-butane: 1H NMR (CDCl3) δ 4.65 (br, 1H), 3.70 (br m, 1H), 1.45 (s, 9H), 1.39 (d, 3H), 1.32 (d, 3H) and 1.18 (d, 3H) ppm.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated
  3. dissolutionThe residue was dissolved in diethyl ether (100 mL)
  4. washwashed with 1N aq. HCl (2×50 mL), water (2×50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and evaporation
  7. customgave a residue that
  8. customwas chromatographed (silica gel, diethyl ether/hexane (3/1))

Sources & evidence

ORD record
ord-539d3a22969342f18176a0345d2e512c
Source dataset
uspto-grants-1998_06
Patent number
US05763474

Reaction notes

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