Methyl morpholine oxide → 5-Indanecarboxaldehyde

HRID 1792147Notes

Reaction equation

HRID 1792147 reaction equation
C[N+]1([O-])[CH2:7][CH2:6][O:5]CC1.N1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C@H]1C(O)=O>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:11]1[C:12]2[C:17](=[CH:18][C:7]([CH:6]=[O:5])=[CH:14][CH:13]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxide2×HCID 2733226(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 1216245-IndanecarboxaldehydeYield 82%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of the alcohol (370 mg, 2.5 mmol) in dichloromethane (10 mL) was stirred at room temperature. N-Methylmorpholine-N-oxide (307 mg, 2.62 mmol) and powdered 4 Å molecular sieves (˜1 g) were added and the mixture was stirred under Ar for 30 minutes. Tetrapropylammonium perruthenate (44 mg, 0.12 mmol) was added in one portion and stirring was continued for 30 minutes. Tic indicated some starting material remaining, so further N-methylmorpholine-N-oxide (100 mg, 0.85 mmol) was added and stirring continued for an additional 30 minutes. The mixture was evaporated onto SiO2 (˜2 g) and purified by flash column chromatography (SiO2, 10% EtOH/Hexane eluent) to afford the aldehyde as a pale yellow oil (299 mg, 82%).

Workup

  1. additionwere added
  2. stirringstirring
  3. waitwas continued for 30 minutes
  4. stirringstirring
  5. waitcontinued for an additional 30 minutes
  6. customThe mixture was evaporated onto SiO2 (˜2 g)
  7. custompurified by flash column chromatography (SiO2, 10% EtOH/Hexane eluent)

Sources & evidence

ORD record
ord-d9fd8deb9f9041d49aa55f11a004bd0c
Source dataset
uspto-grants-2006_07
Patent number
US07074934B2

Reaction notes

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