Nitrogen → tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate hydrochloride

HRID 857166Notes

Reaction equation

HRID 857166 reaction equation
[ClH:1].C([N:9]1[CH2:16][C@@H:15]2[C@@H:11]([CH2:12][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]2)[CH2:10]1)C1C=CC=CC=1.N#N>CO.CCOC(C)=O.[Pd]>[ClH:1].[CH2:12]1[CH:11]2[CH2:10][NH:9][CH2:16][CH:15]2[CH2:14][N:13]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]

Participants

6

Reactant 2

HCID 947NitrogenHCID 69662689(3AS,6AR)-Tert-butyl 5-benzyl-hexahydropyrrolo[3,4-C]pyrrole-2(1H)-carboxylate hcl

Product 1

HCID 21867628tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate hydrochlorideYield 87%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-benzyl-7-(tert-butoxycarbonyl)-3,7-diazabicyclo[3.3.0]-octane hydrochloride (91.1 g, 269 mmol; from step (d) above) in methanol (250 mL) under a N2 atmosphere there was added 10% Pd/C (w/w; 9.8 g). The N2 atmosphere was exchanged for H2 (1 atm of pressure) and the reaction was stirred for 18 h. The reaction was filtered through a pad of cellulose to remove the catalyst. The filtrate was concentrated in vacuo to afford an off-white solid. The solid was slurried in EtOAc and collected. After drying in a vacuum oven for 18 h at 60° C./66.5 Pa (0.5 mm Hg) there was obtained 58.0 g (87%) of the title compound as an off-white solid.

Workup

  1. filtrationThe reaction was filtered through a pad of cellulose
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto afford an off-white solid
  5. customcollected
  6. customAfter drying in a vacuum oven for 18 h at 60° C./66.5 Pa (0.5 mm Hg) there

Sources & evidence

ORD record
ord-7b5dcdce41244360891ae62f59457790
Source dataset
uspto-grants-2006_12
Patent number
US07144914B2

Reaction notes

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