Ammonium Chloride → trans 6-(2,4,5-Trifluorophenyl)-3-[(triisopropylsilyl)oxy]cyclohex-2-en-1-amine

HRID 602941Notes

Reaction equation

HRID 602941 reaction equation
[N:1]([CH:4]1[CH:9]([C:10]2[CH:15]=[C:14]([F:16])[C:13]([F:17])=[CH:12][C:11]=2[F:18])[CH2:8][CH2:7][C:6]([O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])=[CH:5]1)=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].[Cl-].[NH4+]>CCOCC>[F:18][C:11]1[CH:12]=[C:13]([F:17])[C:14]([F:16])=[CH:15][C:10]=1[C@H:9]1[C@H:4]([NH2:1])[CH:5]=[C:6]([O:19][Si:20]([CH:24]([CH3:26])[CH3:25])([CH:27]([CH3:29])[CH3:28])[CH:21]([CH3:22])[CH3:23])[CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 86616049{[3-Azido-4-(2,4,5-trifluorophenyl)cyclohex-1-en-1-yl]oxy}(triisopropyl)silane

Product 1

HCID 67065833trans 6-(2,4,5-Trifluorophenyl)-3-[(triisopropylsilyl)oxy]cyclohex-2-en-1-amine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of {[3-azido-4-(2,4,5-trifluorophenyl)cyclohex-1-en-1-yl]oxy}(triisopropyl)silane (48.2 g) in ether (280 mL) at 0° C. in a three-neck flask (1 L) was added lithium aluminum hydride (1M in ether, 85 mL) while maintaining the temperature below 5° C. The reaction mixture was allowed to warm up to room temperature after completion of addition of the hydride. The mixture was transferred to ice with some saturated aqueous ammonium chloride solution and filtered. The residue was washed with ethyl acetate (1 L), and the organic layer separated, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was chromatographed (silica gel, gradient 10-35% ethyl acetate in heptane) to yield the faster eluting cis- and the slower-eluting trans 6-(2,4,5-trifluorophenyl)-3-[(triisopropylsilyl)oxy]cyclohex-2-en-1-amine.

Workup

  1. temperaturewhile maintaining the temperature below 5° C
  2. filtrationfiltered
  3. washThe residue was washed with ethyl acetate (1 L)
  4. customthe organic layer separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed (silica gel, gradient 10-35% ethyl acetate in heptane)
  9. customto yield the
  10. washfaster eluting cis-

Sources & evidence

ORD record
ord-fc7c0b1f39454db6a82b555359df1392
Source dataset
uspto-grants-2011_03
Patent number
US07906649B2

Reaction notes

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