Potassium Cyanide → tert-butyl (3aR,6aR)-5-[6-bromo-5-(cyanomethyl)-3-pyridinyl]hexahydropyrrolo[3,4-b]pyrrole-1(2H)-carboxylate

HRID 1817014Notes

Reaction equation

HRID 1817014 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:15][C@@H:14]3[C@@H:10]([N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:13]3)[CH2:9]2)=[CH:4][C:3]=1[CH2:23]OS(C)(=O)=O.[C-:29]#[N:30].[K+]>>[Br:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:15][C@@H:14]3[C@@H:10]([N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:13]3)[CH2:9]2)=[CH:4][C:3]=1[CH2:23][C:29]#[N:30]

Participants

3

Reactant 2

HCID 9032Potassium CyanideHCID 86584384HCID 86584384, compound

Product 1

HCID 86584383tert-butyl (3aR,6aR)-5-[6-bromo-5-(cyanomethyl)-3-pyridinyl]hexahydropyrrolo[3,4-b]pyrrole-1(2H)-carboxylateYield 39%

Conditions

Temperature
60 °C

Procedure

The product of Example 66A (0.300 g, 0.630 mmol) in N,N-dimethylfomamide (5 mL) was treated with KCN (61 mg, 0.945 mmol). The mixture was warmed to 60° C. and allowed to stir for 20 hours. The mixture was then concentrated under reduced pressure and the residue purified via chromatography (SiO2, 50% ethyl acetate/hexanes) to provide the title compound (0.100 g, 0.246 mmol, 39% yield). MS (DCI/NH3) m/z 409 (M+H)+.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customthe residue purified via chromatography (SiO2, 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a3f8143cdc594370a6c2a9d7369ffd1e
Source dataset
uspto-grants-2009_10
Patent number
US07598236B2

Reaction notes

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