Cesium carbonate → tert-Butyl 5-[4-(4-cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl]-hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

HRID 857180Notes

Reaction equation

HRID 857180 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH:9]([C:21]1[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=1)[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)(=O)=O.[CH2:29]1[CH:33]2[CH2:34][NH:35][CH2:36][CH:32]2[CH2:31][N:30]1[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38].C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[C:27]([C:24]1[CH:23]=[CH:22][C:21]([CH:9]([O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH2:8][CH2:7][CH2:6][N:35]2[CH2:34][CH:33]3[CH2:29][N:30]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:31][CH:32]3[CH2:36]2)=[CH:26][CH:25]=1)#[N:28]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylateHCID 218675684-(4-Cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl methanesulfonate

Product 1

HCID 21867606tert-Butyl 5-[4-(4-cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl]-hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(4-Cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl methanesulfonate (1.12 g, 2.8 mmol; see step (c) above), tert-butyl hexahydropyrrolo[3,4-c]-pyrrole-2(1H)-carboxylate (0.59 g, 2.8 mmol; see Preparation A above) and Cs2CO3 were mixed in CH3CN (30 mL) and stirred at rt for 3 days. The mixture was then filtered and evaporated. Purification on silica (ethyl acetate:MeOH (9:1) eluant) gave 0.9 g (60%) of the sub-title compound.

Workup

  1. filtrationThe mixture was then filtered
  2. customevaporated
  3. customPurification on silica (ethyl acetate:MeOH (9:1) eluant)

Sources & evidence

ORD record
ord-0c6dcbbebff2421d8459d31370f1e382
Source dataset
uspto-grants-2006_12
Patent number
US07144914B2

Reaction notes

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