4-Bromobenzoyl chloride → HCID 90079356, compound

HRID 1482939Notes

Reaction equation

HRID 1482939 reaction equation
[CH2:1]1[CH:5]2[CH2:6][NH:7][CH2:8][CH:4]2[CH2:3][N:2]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C(N(C(C)C)C(C)C)C.[Br:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1>C(Cl)Cl>[C:12]([O:11][C:9]([N:2]1[CH2:3][CH:4]2[CH:5]([CH2:6][N:7]([C:30](=[O:31])[C:29]3[CH:33]=[CH:34][C:26]([Br:25])=[CH:27][CH:28]=3)[CH2:8]2)[CH2:1]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 685154-Bromobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylate

Product 1

HCID 90079356HCID 90079356, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1.1 tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (0.65 g; 3.06 mmol) is dissolved in 20 ml of DCM. N-Ethyldiisopropylamine for synthesis (1.56 ml; 9.19 mmol) is added and the mixture cooled to 0° C. Now 4-bromobenzoyl chloride for synthesis (0.74 g; 3.37 mmol) is dissolved in 10 ml of DCM and added dropwise to the reaction, followed by stirring at RT for 14 h. The reaction mixture is extracted with 50 ml of water. The organic layer is separated, dried over MgSO4, filtered off and then reduced to dryness under vacuo to afford 1.10 g (90.9%) 5-(4-bromo-benzoyl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester 1 as a slight orange oil.

Workup

  1. additionis added
  2. additionadded dropwise to the reaction
  3. extractionThe reaction mixture is extracted with 50 ml of water
  4. customThe organic layer is separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered off

Sources & evidence

ORD record
ord-d4dadbe6c58643baa6b8a8573e3de501
Source dataset
uspto-grants-2016_08
Patent number
US09416133B2

Reaction notes

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