HCID 86680655, compound → HCID 86680656, compound

HRID 1615415Notes

Reaction equation

HRID 1615415 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][O:13][CH2:12][CH2:11][N:10]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:5][CH:4]=1>C1COCC1.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:4]=[CH:5][C:6]([C@@H:9]2[CH2:14][O:13][CH2:12][CH2:11][N:10]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:7][CH:8]=1)=[O:1]

Participants

4

Reactant 1

HCID 86680655HCID 86680655, compound

Product 1

HCID 86680656HCID 86680656, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (3R)-3-[4-(hydroxymethyl)phenyl]morpholine-4-carboxylate 10 (6 g, 20.45 mmol) in THF (121.4 mL) was added manganese dioxide (17.78 g, 204.5 mmol) and the resulting mixture stirred at rt overnight. The reaction mixture filtered through pad of celite, and washed with EtOAc (3×50 mL). The filtrate was concentrated in vacuo to leave product as a colourless oil (5.54 g, 93% yield), which was used directly in the next step without further purification; 1H NMR (400.0 MHz, DMSO) d 1.39 (9H, s), 3.05 (1H, m), 3.52 (1H, m), 3.71-3.87 (4H, m), 4.28 (1H, m), 5.06 (1H, s), 7.55 (2H, m), 7.93 (2H, m) and 10.00 (1H, s) ppm

Workup

  1. filtrationThe reaction mixture filtered through pad of celite
  2. washwashed with EtOAc (3×50 mL)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e9da2fe3b03c4a949553283dba30213d
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

Loading…