Diisopropylethylamine → HCID 68682015, compound

HRID 1441720Notes

Reaction equation

HRID 1441720 reaction equation
C(O[C:6]([N:8]1[C@:12]2([CH2:16][CH2:15][N:14]([C@H:17]([C:19]([O:21][CH3:22])=[O:20])[CH3:18])[C:13]2=[O:23])[CH2:11][CH2:10][CH2:9]1)=O)(C)(C)C.O1CCOCC1.Cl.C(N(C(C)C)CC)(C)C.BrC[CH:42]=[CH:43][CH2:44][OH:45]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:22][O:21][C:19](=[O:20])[CH:17]([N:14]1[CH2:15][CH2:16][C:12]2([N:8]([CH2:6][CH:42]=[CH:43][CH2:44][OH:45])[CH2:9][CH2:10][CH2:11]2)[C:13]1=[O:23])[CH3:18]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 204431481,4-Dioxane hydrochlorideHCID 53401857HCID 53401857, compoundHCID 68679853HCID 68679853, compound

Product 1

HCID 68682015HCID 68682015, compound

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

82 mg (0.25 mmol) (S,S)-7-(1-methoxycarbonyl-ethyl)-6-oxo-1,7-diaza-spiro[4.4]nonane-1-carboxylic acid tert-butyl ester are stirred at room temperature for three hours in 1 mL of a 4N HCl dioxane solution, evaporated, then taken up in toluene and evaporated again (twice). The residue is taken up in 2 mL dichloromethane and stirred at room temperature for 65 hours in the presence of 74 mg (0.2 mmol) tetrabutylammonium iodide, 0.035 mL (0.2 mmol) diisopropylethylamine and 30 mg (0.2 mmol) 4-bromo-but-2-en-1-ol. The reaction mixture is extracted with EtOAc and saturated aqueous sodium bicarbonate, the combined organic phases washed with brine, evaporated to dryness and the residue column chromatographed (silica gel, EtOAc/EtOH 9:1) to yield the desired product as a thick liquid.

Workup

  1. customevaporated
  2. customevaporated again (twice)
  3. extractionThe reaction mixture is extracted with EtOAc and saturated aqueous sodium bicarbonate
  4. washthe combined organic phases washed with brine
  5. customevaporated to dryness
  6. customthe residue column chromatographed (silica gel, EtOAc/EtOH 9:1)

Sources & evidence

ORD record
ord-a8eed14375624484b0e84870a1ac3103
Source dataset
uspto-grants-2010_02
Patent number
US07655686B2

Reaction notes

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