Hydrochloric Acid → 1-[4-((2R,6S)-2,6-dimethyl-morpholin-4-yl)-2,3-difluoro-5-hydroxymethyl-phenyl]-ethanone

HRID 577811Notes

Reaction equation

HRID 577811 reaction equation
C([SiH2][O:6][C:7](C1C=CC=CC=1)(C1C=CC=CC=1)[C:8]1[C:9]([N:19]2[CH2:24][C@H:23]([CH3:25])[O:22][C@H:21]([CH3:26])[CH2:20]2)=[C:10]([F:18])[C:11]([F:17])=[C:12]([C:14](=[O:16])[CH3:15])[CH:13]=1)(C)(C)C.Cl.O>O1CCOCC1>[CH3:25][C@H:23]1[O:22][C@@H:21]([CH3:26])[CH2:20][N:19]([C:9]2[C:8]([CH2:7][OH:6])=[CH:13][C:12]([C:14](=[O:16])[CH3:15])=[C:11]([F:17])[C:10]=2[F:18])[CH2:24]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178466840HCID 178466840, compound2×

Product 1

HCID 866580491-[4-((2R,6S)-2,6-dimethyl-morpholin-4-yl)-2,3-difluoro-5-hydroxymethyl-phenyl]-ethanone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-((2R,6S)-2,6-dimethyl-morpholin-4-yl)-2,3-difluoro-phenyl]-ethanone (Intermediate 9, 7.2 g, 28 mmol) and 4N HCl in dry dioxane (75 mL) was stirred at room temperature for 12 hours. The reaction mixture was treated with cold water (20 mL) and extracted with ethyl acetate (3×50 mL). The combined organic phases combined were dried (Na2SO4) and concentrated. The residue was purified over a silica gel flash column using a gradient of ethyl acetate in pet. ether to give the title compound as yellow solid.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. dry with materialThe combined organic phases combined were dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified over a silica gel flash column

Sources & evidence

ORD record
ord-c8e25a50a2914d80ab162bd3939a428c
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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