N-(4-Hydroxycyclohexyl)isobutyramide → 2-Methyl-N-(4-oxocyclohexyl)propanamide

HRID 545498Notes

Reaction equation

HRID 545498 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:12][CH:13]1[CH2:18][CH2:17][CH:16]([NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])[CH2:15][CH2:14]1>C(Cl)Cl>[O:12]=[C:13]1[CH2:14][CH2:15][CH:16]([NH:19][C:20](=[O:24])[CH:21]([CH3:22])[CH3:23])[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 21533977N-(4-Hydroxycyclohexyl)isobutyramideHCID 178418287HCID 178418287, compound

Product 1

HCID 215339942-Methyl-N-(4-oxocyclohexyl)propanamideYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add pyridinium chlorochromate (561.6 g, 2.61 mol) to N-(4-hydroxycyclohexyl)isobutyramide (321.8 g, 1.74 mol) in CH2Cl2 (8000 mL) and stir mechanically for 24 h under nitrogen. Add silica gel (2000 g), stir, and filter through a silica pad (6000 g). Elute with CH2Cl2 followed by 75-100% EtOAc/hexanes to obtain 210 g of a light brown solid (66%/o). MS (ES): m/z 184 (M+1); 1H NMR(DMSO-d6): δ 5.54 (br s, NH), 4.27 (septet, 1H), 2.20-2.60 (m, 7H), 1.78 (m, 2H), 1.15 (d, 6H).

Workup

  1. stirringAdd silica gel (2000 g), stir
  2. filtrationfilter through a silica pad (6000 g)
  3. washElute with CH2Cl2

Sources & evidence

ORD record
ord-f7d5d823753a4906a11cdc975afb34e5
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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