Hydrochloric Acid → (2S,3S,5R)-2-(3,4-difluorophenyl)-3,5-dimethyl-2-morpholinol hydrochloride

HRID 265234Notes

Reaction equation

HRID 265234 reaction equation
Br.[F:2][C:3]1[CH:4]=[C:5]([C@:10]2([OH:18])[O:15][CH2:14][C@@H:13]([CH3:16])[NH:12][C@H:11]2[CH3:17])[CH:6]=[CH:7][C:8]=1[F:9].[OH-].[Na+].[ClH:21]>O.CCOCC>[ClH:21].[F:2][C:3]1[CH:4]=[C:5]([C@:10]2([OH:18])[O:15][CH2:14][C@@H:13]([CH3:16])[NH:12][C@H:11]2[CH3:17])[CH:6]=[CH:7][C:8]=1[F:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67706270(2S, 3S, 5R)-2-(3,4difluorophenyl)-3,5-dimethyl-2-morpholinol hydrobromide

Product 1

HCID 67706269(2S,3S,5R)-2-(3,4-difluorophenyl)-3,5-dimethyl-2-morpholinol hydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of (2S,3S,5R)-2-(3,4-difluorophenyl)-3,5-dimethyl-2-morpholinol hydrobromide (4.85 g, 0.015 mole) in water was basified with 40% aqueous sodium hydroxide and extracted with diethyl ether. The diethyl ether layers were combined, washed with brine, dried (potassium carbonate) and concentrated under reduced pressure to yield the free base. The free base was dissolved in ether and treated with ethereal hydrogen chloride. The hydrochloride salt was recrystallized from ethanol-diethyl ether mixtures to give 3.26 g of (2S,3S,5R)-2-(3,4-difluorophenyl)-3,5-dimethyl-2-morpholinol hydrochloride as a white solid. m.p. 223°-225° C. dec.

Workup

  1. extractionextracted with diethyl ether
  2. washwashed with brine
  3. dry with materialdried (potassium carbonate)
  4. concentrationconcentrated under reduced pressure
  5. customto yield the free base
  6. customThe hydrochloride salt was recrystallized from ethanol-diethyl ether mixtures

Sources & evidence

ORD record
ord-532616588e714140bcc3cc25d8c7bfa4
Source dataset
uspto-grants-1997_07
Patent number
US05648347

Reaction notes

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