Hydrogen Peroxide → HCID 86646671, compound

HRID 1799216Notes

Reaction equation

HRID 1799216 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15](B3OC(C)(C)C(C)(C)O3)[CH:14]=2)[CH2:10][C:9]1=[O:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:30]O>ClCCl.[Cl-].[NH4+]>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C@@H:11]2[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:9](=[O:29])[CH2:10]2)=[CH:14][C:15]=1[OH:30]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 86646672HCID 86646672, compound

Product 1

HCID 86646671HCID 86646671, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

One an one-half (1.5 g, 3.56 mmol) of (4R)-tert-butyl-4-[4-chloro-3-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2yl))phenyl]-2-oxopyrrolidinecarboxylate was dissolved in 10 mL dichloromethane. To this solution, 3 equiv. of 35% hydrogen peroxide (10.68 mmol) was added dropwise. The reaction mixture was stirred overnight at room temperature. The mixture was diluted with saturated ammonium chloride aqueous solution and extracted with dichloromethane (3 times). The combined organic layers were dried over Na2SO4 and concentrated to dryness to provide tert-butyl (4R)-4-(4-chloro-3-hydroxyphenyl)-2-oxopyrrolidinecarboxylate (68a) as a clear oil (1.2 g, 95% yield). 1H-NMR (400 MHz, CD3OD): δ 2.63-2.69 (dd, J=17.2, 9.2 Hz, 1H), 2.80-2.87 (dd, J=17.2, 8.4 Hz, 1H), 3.47-3.54 (m, 1H), 3.61-3.66 (m, 1H), 4.12-4.11 (t, J=2.4 Hz, 1H), 7.24-7.22 (d, J=8.0 Hz, 1H), 6.82-6.82 (d, J=2.0 Hz, 1H), 6.73-6.75 (d, J=2.0 Hz, 1H); MS (ESI) m/z 334.01 (M+Na)+.

Workup

  1. extractionextracted with dichloromethane (3 times)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-de019c640cbd491286bc045c54a0fca2
Source dataset
uspto-grants-2013_01
Patent number
US08344028B2

Reaction notes

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