Triethylamine → 2-Benzyl 5-(tert-butyl) tetrahydropyrrolo[3,4-C]pyrrole-2,5(1H,3H)-dicarboxylate

HRID 857173Notes

Reaction equation

HRID 857173 reaction equation
Cl.[CH2:2]1[CH:6]2[CH2:7][NH:8][CH2:9][CH:5]2[CH2:4][N:3]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(N([CH2:22][CH3:23])CC)C>C(Cl)(Cl)Cl>[CH2:7]1[CH:6]2[CH2:2][N:3]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4][CH:5]2[CH2:9][N:8]1[C:10]([O:12][CH2:13][C:23]1[CH:22]=[CH:2][CH:6]=[CH:5][CH:4]=1)=[O:11]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 21867628tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate hydrochloride

Product 1

HCID 218675632-Benzyl 5-(tert-butyl) tetrahydropyrrolo[3,4-C]pyrrole-2,5(1H,3H)-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate hydrochloride (10 g, 0.04 mol; see Preparation A above) and triethylamine (14 mL, 0.1 mol) were mixed in CHCl3 (100 mL). N-benzyloxy-carbonyloxy succinimide (11 g, 0.044 mol), dissolved in CHCl3 (100 mL), was added at 0–5° C. The mixture was allowed to slowly reach room temperature and was stirred at rt for 5 h. The reaction mixture was washed with water, dried (Na2SO4) and evaporated, giving the sub-title compound in quantitative yield.

Workup

  1. additionwas added at 0–5° C
  2. customwas allowed to slowly reach room temperature
  3. washThe reaction mixture was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-69286a619b6d4fc1b4c41a16c9bd7943
Source dataset
uspto-grants-2006_12
Patent number
US07144914B2

Reaction notes

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