Ethyl Acetate → HCID 117778323, compound

HRID 1500499Notes

Reaction equation

HRID 1500499 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][N:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:5]=[CH:6][CH:7]=1.[C:24]1(B2OC(C)(C)C(C)(C)O2)[CH2:28][CH2:27][CH2:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C(O)C.O>[C:12]([O:11][C:10]([N:9]([CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:24]2[CH2:28][CH2:27][CH2:26][CH:25]=2)[CH:3]=1)[C:17](=[O:18])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:16])([CH3:15])([CH3:14])[CH3:13]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 154866112-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 18331463HCID 18331463, compound

Product 1

HCID 117778323HCID 117778323, compoundYield 94.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Tert-butyl N-[(3-bromophenyl)methyl]-N-tert-butoxycarbonylcarbamate (5.40 g) was dissolved in a mixed solvent of toluene (150 mL), ethanol (100 mL), and water (100 mL). To the solution, 2-(cyclopenten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.26 g), tetrakis(triphenylphosphine) palladium complex (1.62 g), and sodium carbonate (4.45 g) were added at room temperature, and the mixture was then heated to reflux for 19 hours. The reaction solution was cooled to room temperature, and ethyl acetate was then added thereto for separation into organic and aqueous layers. The organic layer was washed with water and concentrated under reduced pressure, and the obtained residue was then purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate) to obtain the title compound (4.92 g).

Workup

  1. temperaturethe mixture was then heated
  2. temperatureto reflux for 19 hours
  3. customfor separation into organic and aqueous layers
  4. washThe organic layer was washed with water
  5. concentrationconcentrated under reduced pressure
  6. customthe obtained residue was then purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-29612bae8bcc4f438608f252efe44c9a
Source dataset
uspto-grants-2015_12
Patent number
US09206168B2

Reaction notes

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