Methyl morpholine oxide → HCID 57473823, compound

HRID 576591Notes

Reaction equation

HRID 576591 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]([CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1)[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:15][CH2:16][CH2:17][OH:18])([CH:12]([CH3:14])[CH3:13])[C:8]1=[O:19].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:28][C:2]([F:1])([F:27])[C:3]1[CH:4]=[C:5]([CH:20]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:22]=1)[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:15][CH2:16][CH:17]=[O:18])([CH:12]([CH3:13])[CH3:14])[C:8]1=[O:19]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 57473822HCID 57473822, compound

Product 1

HCID 57473823HCID 57473823, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3,5-bis(trifluoromethyl)benzyl)-3-(3-hydroxypropyl)-3-isopropylpyrrolidin-2-one (1.1 g, approximately 2.67 mmol) in CH2Cl2 (27 mL) was added tetra-n-propylammonium perruthenate (47 mg, 0.134 mmol), N-methylmorpholine N-oxide (0.626 g, 5.35 mmol) and 4 angstrom molecular sieves (0.31 g). After 30 minutes stirring, the solution was filtered through celite and concentrated to provide 3-(1-(3,5-bis(trifluoromethyl)benzyl)-3-isopropyl-2-oxopyrrolidin-3-yl)propanal as an impure dark oil that was used in step 3 without further purification. LC/MS [M+H]+=410.15. HPLC tR=1.96 min [Waters Sunfire C18 4.6×50 mm column, 3 min gradient from 10/90/0.1 MeOH/H2O/TFA to 90/10/0.1 MeOH/H2O/TFA at 4 mL/min flow rate].

Workup

  1. filtrationthe solution was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b67fd659d7ca42309ca2c031f50b4246
Source dataset
uspto-grants-2015_05
Patent number
US09040526B2

Reaction notes

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