Water → tert-Butyl 5-(2-trifluoromethylbenzoyl)-3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyrrole-2-carboxylate

HRID 1186775Notes

Reaction equation

HRID 1186775 reaction equation
Cl.[CH2:2]1[C:6]2[CH2:7][NH:8][CH2:9][C:5]=2[CH2:4][N:3]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(N(CC)CC)C.[F:24][C:25]([F:36])([F:35])[C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](Cl)=[O:29].O>C(Cl)Cl>[F:24][C:25]([F:35])([F:36])[C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28]([N:8]1[CH2:7][C:6]2[CH2:2][N:3]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4][C:5]=2[CH2:9]1)=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 45792433tert-butyl 1H,2H,3H,4H,5H,6H-pyrrolo(3,4-c)pyrrole-2-carboxylate hydrochloride

Product 1

HCID 58075189tert-Butyl 5-(2-trifluoromethylbenzoyl)-3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3,4,5,6-tetrahydro-1H-pyrrolo[3,4-C]pyrrole-2-carboxylate hydrochloride (30 g, 121.6 mmol) was suspended in 700 ml of methylene chloride, triethylamine (50.7 ml, 364.8 mmol) was added with ice bath cooling, and 2-(trifluoromethyl)benzoyl chloride (25.22 ml, 171.2 mmol) was slowly added dropwise. The brown suspension was stirred for 2 h, in the course of which it was allowed to come to RT. The reaction mixture was admixed with water, and the organic phase was removed, dried and concentrated by rotary evaporation. The crude product (56.8 g) was converted further without purification.

Workup

  1. temperaturecooling
  2. customto come to RT
  3. customthe organic phase was removed
  4. customdried
  5. concentrationconcentrated by rotary evaporation
  6. customThe crude product (56.8 g) was converted further without purification

Sources & evidence

ORD record
ord-c8919835bd52435098e98114a3b10906
Source dataset
uspto-grants-2014_03
Patent number
US08673917B2

Reaction notes

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