Triethylamine → HCID 49834379, compound

HRID 1627064Notes

Reaction equation

HRID 1627064 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[CH:8][C:7]=1[C:21]([F:24])([F:23])[F:22].C(N(CC)CC)C.[C:33]1(=[O:38])[CH2:37][CH2:36][CH:35]=[CH:34]1>O1CCOCC1.[Cl-].[Na+].O>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C@H:35]2[CH2:36][CH2:37][C:33](=[O:38])[CH2:34]2)=[CH:8][C:7]=1[C:21]([F:22])([F:23])[F:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 135882-Cyclopenten-1-oneHCID 49834377HCID 49834377, compound

Product 1

HCID 49834379HCID 49834379, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
25 °C

Procedure

[Rh(S-BINAP)(nbd)]BF4 (0.03 mmol) and 3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-trifluoromethyl-phenyl]-propionic acid methyl ester (preparation 2) (1.5 mmol) were added to a 25 mL-flask containing a magnetic stirring bar and a septum inlet. The flask was flashed with argon. Triethylamine (1.5 mmol) and 2-cyclopenten-1-one (1.0 mmol) dissolved in aqueous 1,4-dioxane (6/1, 3 mL) were then added. The mixture was stirred for 6 h at 25° C. Brine was added, the mixture was extracted with ethyl acetate, and the solvents were removed in vacuo to afford the title compound.

Workup

  1. additioncontaining a magnetic stirring bar and a septum inlet
  2. additionwere then added
  3. extractionthe mixture was extracted with ethyl acetate
  4. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-39842729bd6c4b0a8d4b50206b3b1f95
Source dataset
uspto-grants-2014_07
Patent number
US08785494B2

Reaction notes

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