Sodium Sulfate → (2R,3R)-4-benzyl-3-ethyl-2-methylmorpholine

HRID 81161Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[C@H:19]([CH2:20][CH3:21])[C@@H:18]([CH3:22])[O:17][CH2:16][C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH2:7]([N:14]1[CH2:15][CH2:16][O:17][C@H:18]([CH3:22])[C@H:19]1[CH2:20][CH3:21])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 70 °C

Procedure

LiAlH4 (217 mg, 37.95 mmol) was added to a solution of (5R,6R)-4-benzyl-5-ethyl-6-methylmorpholin-3-one (200 mg, 0.85 mmol) in THF (10 mL). The reaction mixture was heated at 70° C. for 3 hours and then cooled to 0° C. At 0° C. was added aqueous sodium sulfate (15 mL). The mixture was stirred at room temperature for 10 minutes, and the white solid was removed by filtration. The filtrate was extracted with EtOAc (3×15 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification of the residue on a silica gel column (0 to 30% EtOAc/hexanes) afforded (2R,3R)-4-benzyl-3-ethyl-2-methylmorpholine. MS APCl calc'd for C14H21NO [M+H]+ 220. found 220.

Workup

temperaturecooled to 0° C
customthe white solid was removed by filtration
extractionThe filtrate was extracted with EtOAc (3×15 mL)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification of the residue on a silica gel column (0 to 30% EtOAc/hexanes)

Sources & evidence

ORD record: ord-643c542a511b43878818d39f14eeb34f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846657B2

Reaction notes

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