Potassium Carbonate → tert-Butyl 5-{3-[(4-cyanophenyl)amino]propyl}hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

HRID 857185Notes

Reaction equation

CC1C=CC(S(O[CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=2)(=O)=O)=CC=1.[CH2:24]1[CH:28]2[CH2:29][NH:30][CH2:31][CH:27]2[CH2:26][N:25]1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].C([O-])([O-])=O.[K+].[K+]>CC#N>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([NH:15][CH2:14][CH2:13][CH2:12][N:30]2[CH2:29][CH:28]3[CH2:24][N:25]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:26][CH:27]3[CH2:31]2)=[CH:21][CH:20]=1)#[N:23]

Participants

Conditions

Temperature: 50 °C

Procedure

3-(4-Cyanoanilino)propyl 4-methylbenzenesulfonate (1.98 g, 6 mmol; see step (b) above), and tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (1.49 g, 6 mmol; see Preparation A above) was mixed with K2CO3 (1.93 g, 14 mmol) and CH3CN (100 mL) and then stirred at 50° C. overnight. The solvent was evaporated and the product was purified by chromatography on silica (DCM:MeOH (20:1)) to give 1.83 g (82%) of the sub-title compound.

Workup

customPreparation A above)
customThe solvent was evaporated
customthe product was purified by chromatography on silica (DCM:MeOH (20:1))

Sources & evidence

ORD record: ord-d635304f0f7b4969a10faf5fc7742f50
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144914B2

Reaction notes

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