Methyl morpholine oxide → HCID 22612175, compound

HRID 844080Notes

Reaction equation

HRID 844080 reaction equation
[OH:1][C:2]([C:5]1[CH:33]=[CH:32][C:8]([CH2:9][NH:10][C:11](=[O:31])[C:12]2[CH:17]=[CH:16][CH:15]=[N:14][C:13]=2[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([OH:30])[C:26]([F:29])([F:28])[F:27])[CH:20]=2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[OH:1][C:2]([C:5]1[CH:33]=[CH:32][C:8]([CH2:9][NH:10][C:11](=[O:31])[C:12]2[CH:17]=[CH:16][CH:15]=[N:14][C:13]=2[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25](=[O:30])[C:26]([F:28])([F:29])[F:27])[CH:20]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 22612375HCID 22612375, compound

Product 1

HCID 22612175HCID 22612175, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-[4-(1-Hydroxy-1-methyl-ethyl)-benzyl]-2-[3-(2,2,2-trifluoro-1-hydroxy-ethyl)-phenoxy]-nicotinamide (0.520 grams, 1.13 mmole), NMO (0.192 grams, 1.7 mmole) and 4 Å molecular sieves (0.5 g) in methylene chloride (15 ml) was added TPAP (0.020 grams, 0.06 mmole) and stirred at room temperature for 1 hour. The mixture was filtered through celite, washed with methylene chloride. The filtrate was diluted with 150 ml methylene chloride, washed with water, dried over MgSO4, filtered and concentrated under reduced pressure to give an oil which was purified by chromatography on silica eluting with 2.5% methanol methylene chloride to give a foam (0.506 g). 1H NMR (CDCl3) d 1.54 (6H, s), 4.69 (2H, d), 7.50-7.15 (9H, m), 8.16 (1H, m), 8.64 (1H, m); MS: m/e 458 (M+).

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed with methylene chloride
  3. additionThe filtrate was diluted with 150 ml methylene chloride
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give an oil which
  9. customwas purified by chromatography on silica eluting with 2.5% methanol methylene chloride

Sources & evidence

ORD record
ord-7217d00baac94ae0b5bb99a5e219461a
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

Loading…