1,8-Diazabicyclo(5.4.0)undec-7-ene → 1055306-64-3

HRID 1426689Notes

Reaction equation

HRID 1426689 reaction equation
Br[CH2:2][CH:3]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:5](=[O:15])[C:4]1([F:17])[F:16].N12CCCN=C1CCCCC2>O1CCCC1>[F:17][C:4]1([F:16])[C:3](=[CH2:2])[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[C:5]1=[O:15]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59826883Tert-butyl 4-(bromomethyl)-3,3-difluoro-2-oxopyrrolidine-1-carboxylate

Product 1

HCID 598268761055306-64-3Yield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-(bromomethyl)-3,3-difluoro-2-oxopyrrolidine-1-carboxylate (50.1 g) in tetrahydrofuran (400 mL) was added dropwise 1,8-diazabicyclo[5.4.0]undec-7-ene (25.0 mL) at 0° C. over 15 min. After the completion of the dropwise addition, the mixture was stirred at room temperature for 1 hr. Insoluble materials were filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=4:1). The obtained crystals were washed with diisopropyl ether to give the title compound as colorless crystals (yield 28.1 g, 76%).

Workup

  1. additionAfter the completion of the dropwise addition
  2. filtrationInsoluble materials were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=4:1)
  5. washThe obtained crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-67447c9b1604489a8606fe3d57a37ccc
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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