Diisopropylamine → HCID 66747472, compound

HRID 591201Notes

Reaction equation

HRID 591201 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21]#[N:22])=[CH:16][C:15]=1[O:30][CH3:31].Cl[C:33]([O:35][CH2:36][CH3:37])=[O:34]>C1COCC1.CCOC(C)=O>[CH2:36]([O:35][C:33](=[O:34])[C:20]([CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:21]#[N:22])[C:17]1[CH:18]=[CH:19][C:14]([F:13])=[C:15]([O:30][CH3:31])[CH:16]=1)[CH3:37]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 10928Ethyl chloroformateHCID 66747550HCID 66747550, compoundHCID 178418339Butyllithium

Product 1

HCID 66747472HCID 66747472, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a −78° C. cooled solution of diisopropylamine (5.11 ml, 35.8 mmol) in THF was added n-butyllithium (22.40 ml, 35.8 mmol) and stirred for 1 h while the reaction mixture was allowed to warm up <−40° C. 2-(4-Fluoro-3-methoxyphenyl)-3-phenylpropanenitrile (6.1 g, 23.89 mmol) dissolved in THF was added followed by ethyl chloroformate (3.42 ml, 35.8 mmol). The reaction mixture was stirred over night and was allowed to heat up to room temperature. Evaporated solvents and redissolved in EtOAc, washed with 10% citric acid, water and brine and the combined organic layers were dried over MgSO4, filtered and evaporated to obtain 7.2 g of a yellow oil, that was purified by flash chromatography on 330 g SiO2 using 20% EtOAc in cyclohexene to obtain 18.26 g of the desired product as a pale yellow oil.

Workup

  1. temperatureto warm up <−40° C
  2. additionwas added
  3. stirringThe reaction mixture was stirred over night
  4. washwashed with 10% citric acid, water and brine
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-4e64898f32cf4f00a64b70df83d1c11f
Source dataset
uspto-grants-2016_01
Patent number
US09238619B2

Reaction notes

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