Ammonia → HCID 58932576, compound

HRID 853871Notes

Reaction equation

HRID 853871 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][C:14]#[N:15])[C:7](=O)[C:6]12[O:21][CH2:20][CH2:19][CH2:18][O:17]1.N.C1COCC1>[Ni].CCO>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]3[CH2:12][CH2:13][CH2:14][N:15]=[C:7]3[C:6]3([O:21][CH2:20][CH2:19][CH2:18][O:17]3)[C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 58932566HCID 58932566, compound

Product 1

HCID 58932576HCID 58932576, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 3-(5′-methoxy-2′-oxospiro[1,3-dioxane-2,3′-indol]-1′(2′H)-yl)propanenitrile (1.00 g, 3.47 mmol) and wet Raney Nickel (1.00 g) in 2M EtOH.NH3 (45 mL) and THF (45 mL) was hydrogenated in a Parr Hydrogenation Bottle (250 mL) at 53 lb/in H2 for 20 hr. The mixture was filtered through Celite and the filtrate was poured into a steel pressure vessel and heated at 135° C. for 66 hr. The reaction was cooled to room temperature and concentrated. The crude product was purified on Biotage KP silica gel eluting with a step gradient CH2Cl2/CH3OH/NH4OH (98.5/1/0.5 to 97/2/1) to give the title compound as a tan solid (0.26 g, 27% ). NMR (300 Mz, DMSO-d6): consistent. MS: (API-ES+) 275[M+H].

Workup

  1. customfor 20 hr
  2. filtrationThe mixture was filtered through Celite
  3. additionthe filtrate was poured into a steel pressure vessel
  4. temperatureThe reaction was cooled to room temperature
  5. concentrationconcentrated
  6. customThe crude product was purified on Biotage KP silica gel eluting with a step gradient CH2Cl2/CH3OH/NH4OH (98.5/1/0.5 to 97/2/1)

Sources & evidence

ORD record
ord-a6ccb057dabd46acbf7c041c2f71b106
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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