HCID 22342822, compound → HCID 22342963, compound

HRID 584232Notes

Reaction equation

HRID 584232 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]1[CH2:14][F:15])C1C=CC=CC=1.C([N:23]1[CH2:29][CH:28]([F:30])[CH2:27][O:26][CH2:25][CH2:24]1)C1C=CC=CC=1>CO.[C].[Pd]>[F:15][CH2:14][C@H:9]1[CH2:10][O:11][CH2:12][CH2:13][NH:8]1.[F:30][CH:28]1[CH2:27][O:26][CH2:25][CH2:24][NH:23][CH2:29]1

Participants

6

Reactant 2

HCID 22342822HCID 22342822, compoundHCID 53953167(3R)-4-Benzyl-3-(fluoromethyl)morpholine

Product 2

HCID 22342963HCID 22342963, compoundHCID 54445403793652-02-5

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

The crude mixture (2.2 g) obtained by the previous procedure, which contained mainly (3R)-4-benzyl-3-fluoromethylmorpholine and 4-benzyl-6-fluoroperhydro-1,4-oxazepine, was dissolved in methanol (50 ml). The solution was hydrogenated in the presence of 10% palladium-carbon (200 mg) at room temperature. After 1 hour of stirring, palladium-carbon was removed by filtration and the filtrate was evaporated under reduced pressure. The two isomers were separated by column chromatography using 2% of methanol in dichloromethane as an eluent to give (3R)-3-fluoromethylmorpholine and 6-fluoroperhydro-1,4-oxazepine (the former was less polar). The products were converted to their hydrochloride as a conventional manner using 4N hydrogen chloride in ethyl acetate, respectively.

Workup

  1. custompalladium-carbon was removed by filtration
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe two isomers were separated by column chromatography

Sources & evidence

ORD record
ord-9b992c95e6204eba8af49f390a2ccdb6
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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