Methyl morpholine oxide → HCID 86758776, compound

HRID 1633825Notes

Reaction equation

HRID 1633825 reaction equation
[OH:1][CH2:2][CH:3]1[CH:5]([CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]1[C:14]([O:16][CH2:17][CH3:18])=[O:15].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH:2]([CH:3]1[CH:5]([CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:1]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 86758777HCID 86758777, compound

Product 1

HCID 86758776HCID 86758776, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl (1SR,2SR,3RS) 2-hydroxymethyl-3-(2′-phenylethyl)cyclopropanecarboxylate (1.15 g, 4.6 mmol) in CH2Cl2 (40 mL) at room temperature and under argon, a molecular sieve (4 Å) (2.2 g) was added. After stirring 5 minutes, NMO (0.54 g, 4.6 mmol) and TPAP (0.03 g, 0.09 mmol) were added and the mixture was stirred overnight. Then the reaction mixture was filtered through celite and the solvent was removed to dryness. After purification of the crude by column chromatography using AcOEt/Hexane 1:6 as eluent, 0.7 g (63% yield) of ethyl (1SR,2SR,3RS) 2-formyl-3-(2′-phenylethyl)cyclopropanecarboxylate was obtained as yellow oil.

Workup

  1. stirringthe mixture was stirred overnight
  2. filtrationThen the reaction mixture was filtered through celite
  3. customthe solvent was removed to dryness
  4. customAfter purification of the crude by column chromatography

Sources & evidence

ORD record
ord-5230e39531174daaa435cd3e55f9d54d
Source dataset
uspto-grants-2003_01
Patent number
US06504052B1

Reaction notes

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