Methanol → HCID 59506274, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17](=O)[CH3:18])=[CH:13][C:12]=2[Br:20])[CH:7]=[N:6][CH:5]=1.CO.C([BH3-])#[N:25].[Na+]>>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([NH2:25])[CH3:18])=[CH:13][C:12]=2[Br:20])[CH:7]=[N:6][CH:5]=1Participants
4
Procedure
To a solution of the compound from step 1 (630 mg, 1.79 mmol) in MeOH (30 mL) ammonium acetate (1.39 g, 17.9 mmol) was added. After stirring at ambient temperature overnight sodium cyanoborohydride (135.7 mg, 2.16 mmol) was added and the reaction was refluxed for 6 h. The solvent was evaporated and the solid, dissolved in ethyl acetate, was extracted with water. The organic layer was separated, washed with brine, dried over sodium sulphate, filtered and evaporated to give 606 mg (yield: 96%) of the crude product. LC/MS (method D) (M+H)+: 352