Hydrochloric Acid → HCID 131731314, compound

HRID 2364960Notes

Reaction equation

HRID 2364960 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH:8]([NH2:10])[CH3:9])=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.[C:17]([O:21]C(=O)N[C@@H](C)COC1C=CC(F)=CC=1C(F)(F)F)(C)(C)[CH3:18].[ClH:40]>CO>[ClH:40].[F:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C@@H:8]([NH:10][CH2:18][CH2:17][OH:21])[CH3:9])=[C:4]([C:13]([F:14])([F:15])[F:16])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 70807891HCID 70807891, compoundHCID 77492759HCID 77492759, compound

Product 1

HCID 131731314HCID 131731314, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Synthesis of (2S)-1-[(4-fluoro-2-(trifluoromethyl)phenoxy]propan-2-amine (C7). To a solution of tert-butyl{(2S)-1-[4-fluoro-2-(trifluoromethyl)phenoxy]propan-2-yl}carbamate (C6) (1.87 g, 5.54 mmol) in methanol (10 mL) was added a solution of hydrogen chloride (4 N in 1,4-dioxane, 5 mL). After 4 hours, the reaction mixture was concentrated in vacuo. The resulting residue was taken up in dichloromethane and washed with saturated aqueous sodium bicarbonate solution and water. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0 to 20% methanol in ethyl acetate) afforded the title compound as a yellow liquid. Yield: 785 mg, 3.31 mmol, 60%. LCMS m/z 238.1 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.19 (d, J=6.5 Hz, 3H), 3.35-3.44 (m, 1H), 3.74 (dd, J=8.4, 7.4 Hz, 1H), 3.94 (dd, J=8.5, 4.0 Hz, 1H), 6.93 (dd, J=9.1, 4.2 Hz, 1H), 7.18 (br ddd, J=9, 8, 3 Hz, 1H), 7.30 (dd, J=8.4, 3.1 Hz, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. washwashed with saturated aqueous sodium bicarbonate solution and water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via silica gel chromatography (Gradient: 0 to 20% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-d14ab81616a9484eaa074bb3be53721a
Source dataset
uspto-grants-2014_04
Patent number
US08697673B2

Reaction notes

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