Isopropylamine → HCID 67458243, compound

HRID 625056Notes

Reaction equation

HRID 625056 reaction equation
CS(Cl)(=O)=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:18]O)[C:14]([O:16][CH3:17])=[O:15])=[CH:9][CH:8]=1.FC1C=CC(C(=C)C(OC)=O)=CC=1.[CH:33]([NH2:36])([CH3:35])[CH3:34]>C1COCC1.CCOCC.CCOC(C)=O>[F:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:18][NH:36][CH:33]([CH3:35])[CH3:34])[C:14]([O:16][CH3:17])=[O:15])=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 6363IsopropylamineHCID 31297Methanesulfonyl chlorideHCID 18361954HCID 18361954, compound2×HCID 67458894HCID 67458894, compound

Product 1

HCID 67458243HCID 67458243, compoundYield 99.4%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonyl chloride (1.230 mL, 15.89 mmol) and TEA (4.642 mL, 33.30 mmol) was added to a stirred solution of methyl 2-(4-fluorophenyl)-3-hydroxypropanoate (3 g, 15.14 mmol) in THF (150 mL) at 0° C. under nitrogen. The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 2 days. The resulting suspension was diluted with Et2O (200 mL), filtered and concentrated in vacuo to give a colorless oil containing the intermediate compound, methyl 2-(4-fluorophenyl)acrylate. 1H NMR (CDCl3, 400 MHz) 7.39 (dd, J 8.4 and 5.4 Hz, 2H), 7.04 (app. t, J=8.6 Hz, 2H), 6.36 (s, 1H), 5.87 (s, 1H), 3.83 (s, 1H.) The methyl 2-(4-fluorophenyl)acrylate was taken up into THF (150 mL) and treated with isopropylamine (6.446 mL, 75.68 mmol). The reaction mixture was stirred at room temperature for 2 hours, diluted with EtOAc (200 mL), washed with saturated aqueous bicarbonate (100 mL), dried over Na2SO4 and concentrated in vacuo to give pure methyl 2-(4-fluorophenyl)-3-(isopropylamino)propanoate (3.6 g, 99.39% yield). LCMS (APCI+) [M+H]+ 240.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customto give a colorless oil
  4. stirringThe reaction mixture was stirred at room temperature for 2 hours
  5. washwashed with saturated aqueous bicarbonate (100 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d20c0044c404e51a2ad71790b82f463
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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