Diisopropylethylamine → Tert-butyl 3-(2-hydroxyethyl)-4-(2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)-2-oxoethyl)piperazine-1-carboxylate

HRID 1501970Notes

Reaction equation

HRID 1501970 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[NH:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1.Br[CH2:18][C:19]([C:21]1[C:22]([CH3:31])=[C:23]2[C:27](=[CH:28][CH:29]=1)[C:26](=[O:30])[O:25][CH2:24]2)=[O:20].CCN(C(C)C)C(C)C>O1CCCC1.[Cl-].[Na+].O>[OH:1][CH2:2][CH2:3][CH:4]1[N:9]([CH2:18][C:19]([C:21]2[C:22]([CH3:31])=[C:23]3[C:27](=[CH:28][CH:29]=2)[C:26](=[O:30])[O:25][CH2:24]3)=[O:20])[CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 53407692tert-Butyl 3-(2-hydroxyethyl)piperazine-1-carboxylateHCID 772312635-(2-bromoacetyl)-4-methylisobenzofuran-1(3H)-one

Product 1

HCID 86727041Tert-butyl 3-(2-hydroxyethyl)-4-(2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)-2-oxoethyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

tert-Butyl 3-(2-hydroxyethyl)piperazine-1-carboxylate (6.91 g, 30.0 mmol) and 5-(2-bromoacetyl)-4-methylisobenzofuran-1(3H)-one (6.73 g, 25 mmol) were dissolved in tetrahydrofuran (100 mL) then added Hunig's base (8.73 mL, 50.0 mmol) and stirred at RT overnight. The reaction was poured into brine and extracted with EtOAc (2×). The combined organic layer was dried over Na2SO4, filtered and evaporated to dryness. The crude product was chromatographed through an ISCO Redi-Sep 330 g column and eluted with 5% MeOH/DCM solvent system to the title compound. LC-MS (IE, m/z): 419 [M+1]+.

Workup

  1. extractionextracted with EtOAc (2×)
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product was chromatographed through an ISCO Redi-Sep 330 g column
  6. washeluted with 5% MeOH/DCM solvent system to the title compound

Sources & evidence

ORD record
ord-3810d6379cbf4583a4d68783872d4f0f
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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