HCID 54298093, compound → HCID 54408569, compound

HRID 567858Notes

Reaction equation

HRID 567858 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][CH:23]=1)[O:7][CH2:8][C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])#[N:2]>N.[Ni]>[NH3:2].[NH2:2][CH2:1][CH2:3][C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][CH:23]=1)[O:7][CH2:8][C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15]

Participants

5

Reactant 1

HCID 54298093HCID 54298093, compound

Product 2

HCID 222AmmoniaHCID 54408569HCID 54408569, compoundYield 112.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

A mixture of tert-butyl (2R)-2-{[3-(cyanomethyl)phenoxy]methyl}-1-pyrrolidinecarboxylate (preparation 133) (2.70 g, 8.54 mmol), and Raney® nickel (400 mg) in saturated ethanolic ammonia solution (100 ml), was hydrogentaed at 60 psi and room temperature for 20 hrs. The reaction mixture was filtered through a glass microfibre filter, and the filtrate evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (95:5:0.5 to 90:10:1) to afford the title compound, (1.54 g, 56%).

Workup

  1. filtrationThe reaction mixture was filtered through a glass microfibre
  2. filtrationfilter
  3. customthe filtrate evaporated under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane

Sources & evidence

ORD record
ord-79e57d95c51a43a4ba0b7cd80f12c3de
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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