Triethylsilane → HCID 66853579, compound

HRID 2060794Notes

Reaction equation

HRID 2060794 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]23[CH2:16][CH:15]([OH:17])[CH2:14][CH:13]2[CH2:12][O:11][N:10]3CC2C=CC(OC)=CC=2OC)[CH:5]=[CH:6][C:7]=1[F:8].C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:9]23[CH2:16][CH:15]([OH:17])[CH2:14][CH:13]2[CH2:12][O:11][NH:10]3)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 66852730HCID 66852730, compound

Product 1

HCID 66853579HCID 66853579, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of racemic (3aRS,5RS,6aSR)-6a-(3-bromo-4-fluorophenyl)-1-(2,4-dimethoxybenzyl)hexahydro-1H-cyclopenta[c]isoxazol-5-ol (0.852 g, 1.79 mmol) and triethylsilane (0.624 g, 5.37 mmol) in TFA (4 mL) is heated to 80° C. for 3 h. The reaction is cooled to room temperature and concentrated under reduced pressure to afford a residue that is purified on a SCX column washing sequentially with dichloromethane, methanol and 7 N NH3 in MeOH to give the title compound as racemic mixture (0.57 g, 100%). ES/MS m/e (79Br/81Br) 302, 304 (M+1).

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customto afford a residue that
  4. customis purified on a SCX column
  5. washwashing sequentially with dichloromethane, methanol and 7 N NH3 in MeOH

Sources & evidence

ORD record
ord-95693b81202a4af082e5355d0f8019c5
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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