Water → HCID 57425539, compound

HRID 2354363Notes

Reaction equation

HRID 2354363 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:12]=[CH:11][C:10]([C:13]([NH:22][C:23](=O)OC(C)(C)C)([CH3:21])[C:14](=O)[N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:9][CH:8]=1.O.[F-].[Na+]>C1COCC1.C1(C)C=CC=CC=1>[C:7]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:12]=[CH:11][C:10]([C:13]([NH:22][CH3:23])([CH3:21])[CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5235Sodium FluorideHCID 21226445Aluminium lithium hydrideHCID 57488852HCID 57488852, compound

Product 1

HCID 57425539HCID 57425539, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

LAH (447 mg, 11.8 mmol) was added to a solution of 1,1-dimethylethyl [1-(4-biphenylyl)-1-methyl-2-oxo-2-(1-pyrrolidinyl)ethyl]carbamate (580 mg, 1.47 mmol) in THF (20 ml) at 0° C. under argon. The resulting mixture was then refluxed for 2.5 h. The reaction mixture was then cooled in and ice bath and diluted with toluene (20 ml). Water (847 ul, 47 mmol) was added followed by NaF (1.48 g, 35.3 mmol) and the mixture was stirred at 0° C. for 30 min, filtered and the filter pad was washed with THF. The combined filtrates were concentrated to give 417 mg (96%) as a light brown oil. MS (ES) m/e 295.4 [M+H]+.

Workup

  1. temperatureThe resulting mixture was then refluxed for 2.5 h
  2. temperatureThe reaction mixture was then cooled in and ice bath
  3. filtrationfiltered
  4. washthe filter pad was washed with THF
  5. concentrationThe combined filtrates were concentrated
  6. customto give 417 mg (96%) as a light brown oil

Sources & evidence

ORD record
ord-de0b275ff53c488bbe0e11547d2747cf
Source dataset
uspto-grants-2010_07
Patent number
US07749998B2

Reaction notes

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