Ammonium Hydroxide → HCID 67271025, compound

HRID 602490Notes

Reaction equation

HRID 602490 reaction equation
[C:1]([CH2:3][C@@H:4]1[CH2:8][C@H:7]([NH:9][C:10]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH:21]([CH3:23])[CH3:22])[N:13]=2)=[O:11])[CH2:6][N:5]1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])#[N:2].[OH-].[NH4+]>CO.[Ni]>[NH2:2][CH2:1][CH2:3][C@@H:4]1[CH2:8][C@H:7]([NH:9][C:10]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH:21]([CH3:23])[CH3:22])[N:13]=2)=[O:11])[CH2:6][N:5]1[C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 67269781HCID 67269781, compound

Product 1

HCID 67271025HCID 67271025, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

The mixture of tert-butyl (2S,4S)-2-(cyanomethyl)-4-{[(1-isopropyl-1H-indazol-3-yl)carbonyl]amino}pyrrolidine-1-carboxylate (0.40 g, 0.97 mmol, Step 1 of Example 19) and catalytic Raney-Ni in methanol (16 mL) and 25% ammonium hydroxide (4.0 mL) was stirred under hydrogen (4 atom) at room temperature for 7 h. The mixture was filtered through a pad of Celite. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate 1:1 to dichloromethane/methanol 10:1) to give 115 mg (65%) of the title compound as a colorless oil.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate 1:1 to dichloromethane/methanol 10:1)

Sources & evidence

ORD record
ord-cfbe925b9c944e0e9aa76663e950da4b
Source dataset
uspto-grants-2011_03
Patent number
US07906532B2

Reaction notes

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