Methyl morpholine oxide → HCID 131725146, compound

HRID 496244Notes

Reaction equation

HRID 496244 reaction equation
[C:1]([N:20]1[CH2:34][CH2:33][CH:32]([OH:35])[C@H:21]1[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:1]([N:20]1[CH2:34][CH2:33][C:32](=[O:35])[C@H:21]1[C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 131725147HCID 131725147, compound

Product 1

HCID 131725146HCID 131725146, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-trityl-3-hydroxy-(L)-proline, benzyl ester (8.8 g, 19 mmol) in CH2Cl2 (50 mL) was added 4-methylmorpholine N-oxide (4.5 g, 38 mmol) and 3Å molecular sieves (3 g). After stirring at rt for 15 min, the reaction mixture was cooled to 0° C., and was added tetrapropylammonium perruthenate (1.0 g, 2.8 mmol). After stirring at rt for 15 min, the reaction mixture was filtered through a pad of silica gel, and the filtrate was concentrated in vacuo to dryness. The residue was dissolved in Et2O (100 mL), and was filtered through a pad of silica gel. The filtrate was concentrated in vacuo to dryness to yield N-trityl-3-keto-(L)-proline, benzyl ester (6.5 g, 74%).

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. stirringAfter stirring at rt for 15 min
  3. filtrationthe reaction mixture was filtered through a pad of silica gel
  4. concentrationthe filtrate was concentrated in vacuo to dryness
  5. dissolutionThe residue was dissolved in Et2O (100 mL)
  6. filtrationwas filtered through a pad of silica gel
  7. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-dd351716d4794c27a94d116727d2a591
Source dataset
uspto-grants-2005_09
Patent number
US06943180B2

Reaction notes

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