Pivaloyl chloride → HCID 68614758, compound

HRID 643706Notes

Reaction equation

HRID 643706 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][C:11]1([OH:16])[CH2:15][CH2:14][CH2:13][CH2:12]1.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>C(OCC)(=O)C>[Br:8][C:6]1[CH:5]=[CH:4][C:3]([NH:9][CH2:10][C:11]2([OH:16])[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:2]([NH:1][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:7]=1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 65103218HCID 65103218, compound

Product 1

HCID 68614758HCID 68614758, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-([(2-amino-4-bromophenyl)amino]methyl)cyclopentanol (Step B, 1.3 g, 4.15 mmol) in ethyl acetate (100 mL) was added pivaloyl chloride (511 mg, 4.15 mmol) at room temperature. After stirring for 2 h at room temperature, the mixture was quenched with saturated sodium hydrogen carbonate aqueous solution. The mixture was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 as eluent) to afford the title compound (1.3 g, 75%) as a beige amorphous.

Workup

  1. customthe mixture was quenched with saturated sodium hydrogen carbonate aqueous solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 as eluent)

Sources & evidence

ORD record
ord-2b76ea0856494de0aaeecb946f5be987
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

Loading…