Hydrochloric Acid → 4-[1-(3,4-Dimethoxyphenoxy)-4-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-ylbutyl]benzonitrile

HRID 857181Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([O:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=2)[CH2:10][CH2:11][CH2:12][N:13]2[CH2:17][CH:16]3[CH2:18][N:19](C(OC(C)(C)C)=O)[CH2:20][CH:15]3[CH2:14]2)=[CH:5][CH:4]=1)#[N:2].Cl>C(OCC)(=O)C>[CH3:38][O:37][C:31]1[CH:30]=[C:29]([CH:34]=[CH:33][C:32]=1[O:35][CH3:36])[O:28][CH:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[CH2:10][CH2:11][CH2:12][N:13]1[CH2:17][CH:16]2[CH:15]([CH2:20][NH:19][CH2:18]2)[CH2:14]1

Participants

Conditions

Temperature: 0 °C

Procedure

tert-Butyl 5-[4-(4-cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl]hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (0.9 g, 1.7 mmol; from step (d) above) was dissolved in ethyl acetate (25 mL). The solution was cooled to 0° C. Ethyl acetate (25 mL) saturated with gaseous HCl was added and the mixture was stirred at rt for 4 h. The mixture was evaporated and then dissolved in CH3CN. K2CO3 (1 g) and water (0.05 mL) were added and the mixture was stirred for 2 h. The salts were filtered of and the solvent was evaporated, giving 0.71 g (100%) of the title compound.

Workup

customThe mixture was evaporated
dissolutiondissolved in CH3CN
additionK2CO3 (1 g) and water (0.05 mL) were added
stirringthe mixture was stirred for 2 h
filtrationThe salts were filtered of and the solvent
customwas evaporated

Sources & evidence

ORD record: ord-ca80d05a25574ac2b4e2f2441bf35325
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144914B2

Reaction notes

Loading…