HCID 18694249, compound → HCID 70287160, compound

HRID 1870905Notes

Reaction equation

HRID 1870905 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][C:10]=3[O:9][CH2:8]2)[NH:16][CH2:15][CH2:14]4)[CH2:4][CH2:3]1>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:11]3[CH2:12][C:13]4[C:17](=[CH:18][C:10]=3[O:9][CH2:8]2)[N:16]=[CH:15][CH:14]=4)[CH2:4][CH2:3]1.[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:11]3[CH2:12][C:13]4[C:17](=[CH:18][C:10]=3[O:9][CH2:8]2)[N:16]=[CH:15][CH:14]=4)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 18694249HCID 18694249, compound

Product 1

HCID 70287160HCID 70287160, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 1'-methyl-2,3,5,6-tetrahydrospiro[furo[3,2-f]indole-3,4'-piperidine] (D67, 1.0 g, 4.1 mmole) in dichloromethane (70 ml) at room temp. under argon was treated with manganese dioxide (0.68 g, 8.2 mmole). The mixture was stirred for 18 hours, then additional manganese dioxide was added (0.30 g, 2.4 mnmole). The mixture was stirred for an additional 24 hours, then filtered through a pad of kieselguhr and the filtrate concentrated under vacuum. The two components present were separated by chromatography on neutral alumina. Elution with ether gave the title compound as a white solid (0.41 g, 41%), further elution with ethyl acetate gave the second component.

Workup

  1. stirringThe mixture was stirred for an additional 24 hours
  2. filtrationfiltered through a pad of kieselguhr
  3. concentrationthe filtrate concentrated under vacuum
  4. customThe two components present were separated by chromatography on neutral alumina
  5. washElution with ether
  6. customgave
  7. washthe title compound as a white solid (0.41 g, 41%), further elution with ethyl acetate
  8. customgave the second component

Sources & evidence

ORD record
ord-153022b48be04cd7aa189dbeea7e2cfb
Source dataset
uspto-grants-2000_08
Patent number
US06100272

Reaction notes

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