Methyl morpholine oxide → HCID 23000729, compound

HRID 397655Notes

Reaction equation

HRID 397655 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10]([N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[C:19]1[N:23]=[C:22]([CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([CH2:32][OH:33])=[CH:28][CH:27]=2)[O:21][N:20]=1)(=[O:12])=[O:11].C[N+]1([O-])CCOCC1>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.C(#N)C.ClCCl>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10]([N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[C:19]1[N:23]=[C:22]([CH2:24][O:25][C:26]2[CH:27]=[CH:28][C:29]([CH:32]=[O:33])=[CH:30][CH:31]=2)[O:21][N:20]=1)(=[O:12])=[O:11]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 23000781HCID 23000781, compound

Product 1

HCID 23000729HCID 23000729, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

Tetrapropylammonium perruthenate (14.4 mg) was added to a stirred suspension of 4-(3-[1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)phenylmethanol (384 mg) [see Preparation 21], N-methylmorpholine oxide (166 mg) and 4 Å molecular sieves in 10% v/v acetonitrile/dichloromethane (4 ml). The reaction mixture was stirred for 1 hour after which time the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with ethyl acetate to afford 4-(3-[1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)benzaldehyde (342 mg).

Workup

  1. customwas removed under reduced pressure
  2. customThe crude product was purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-21e7a70c8bf7433eb1a9053a0842413e
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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