Trimethylamine oxide dihydrate → HCID 59165782, compound

HRID 1664767Notes

Reaction equation

HRID 1664767 reaction equation
[OH2:1].[OH2:2].C[N+]([O-])(C)C.[NH:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]2([CH2:20][CH:19]=[CH:18][CH2:17]2)[C:9]1=[O:21]>ClCCl.[Os](=O)(=O)(=O)=O>[OH:1][CH:18]1[CH:19]([OH:2])[CH2:20][C:10]2([C:11]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:8][C:9]2=[O:21])[CH2:17]1

Participants

5

Reactant 2

HCID 198430Trimethylamine oxide dihydrateHCID 59165783spiro[cyclopent-3-ene-1,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Product 1

HCID 59165782HCID 59165782, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of trimethylamine-N-oxide dihydrate (408 mg, 3.67 mmol) and spiro[cyclopent-3-ene-1,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (622 mg, 3.34 mmol) in dichloromethane (115 mL) was added osmium tetroxide (25 uL of 2.5% solution in 2-methyl-2-propanol). After 24 h the reaction mixture was concentrated. The crude product was loaded onto a silica gel chromatography column with a minimal amount of methanol and eluted with a gradient of 5 to 20% methanol:dichloromethane to give the title compound (0.63 g). MS: m/z 221.0 (M+1).

Workup

  1. concentrationAfter 24 h the reaction mixture was concentrated
  2. washeluted with a gradient of 5 to 20% methanol

Sources & evidence

ORD record
ord-512b00fe684f4bd4982161f57d46db0f
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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