Acetic Acid → 2,3-Dihydro-1'-methylspiro[furo[2,3-f]indole-3,4'-piperidine]

HRID 1741034Notes

Reaction equation

HRID 1741034 reaction equation
[C:1]([CH2:3][C:4]1[C:9]([N+:10]([O-])=O)=[CH:8][C:7]2[C:13]3([CH2:20][O:21][C:6]=2[CH:5]=1)[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)#N.O.C(O)(=O)C>[Pd].C(O)C>[CH3:19][N:16]1[CH2:17][CH2:18][C:13]2([C:7]3[CH2:8][C:9]4[C:4]([CH:3]=[CH:1][N:10]=4)=[CH:5][C:6]=3[O:21][CH2:20]2)[CH2:14][CH2:15]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 186900676-(Cyanomethyl)-2,3-dihydro-1'-methyl-5-nitrospiro[benzofuran-3,4'-piperidine]

Product 1

HCID 701980042,3-Dihydro-1'-methylspiro[furo[2,3-f]indole-3,4'-piperidine]Yield 10%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-(Cyanomethyl)-2,3-dihydro-1'-methyl-5-nitrospiro[benzofuran-3,4'-piperidine] (D6, 0.35 g, 1.2 mmol) was hydrogenated at 50 psiH2 over 10% palladium on charcoal (0.30 g) in a mixture of ethanol (18 ml), water (2 ml) and acetic acid (0.15 ml) for 24 h. Catalyst was filtered off onto kieselguhr, and the filtrate was evaporated to dryness. Chromatography on silica gel, eluting with 0-12% methanol/chloroform (gradient) gave the title compound (0.020 g, 10%) as a pale orange solid.

Workup

  1. filtrationCatalyst was filtered off onto kieselguhr
  2. customthe filtrate was evaporated to dryness
  3. washChromatography on silica gel, eluting with 0-12% methanol/chloroform (gradient)

Sources & evidence

ORD record
ord-816466d8edf8447586ccbe183944ff26
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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