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Formic Acid → (1RS,2SR,6RS,7SR,8RS)-8-(3-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione

HRID 407858
Notes
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Reaction equation

HRID 407858 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[CH:3]=1.N1CCCCC1.[CH3:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[C:17]=1[CH:24]1[C:32](=[O:33])[CH:31]2[CH:26]([CH:27]3[O:34][CH:30]2[CH:29]=[CH:28]3)[C:25]1=[O:35].C(O)=O>CN(C)C=O.ClCCl.O>[F:1][C:2]1[CH:3]=[C:4]([CH:29]2[CH2:28][CH:27]3[O:34][CH:30]2[CH:31]2[CH:26]3[C:25](=[O:35])[CH:24]([C:17]3[C:18]([CH3:23])=[CH:19][C:20]([CH3:22])=[CH:21][C:16]=3[CH3:15])[C:32]2=[O:33])[CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 284Formic AcidHCID 8082PiperidineHCID 707251-Fluoro-3-iodobenzeneHCID 67283862(1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-en-3,5-dione

Product 1

HCID 67284052(1RS,2SR,6RS,7SR,8RS)-8-(3-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione

Reagents, catalysts & solvents

3
HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Bis(triphenylphosphine)palladium diacetate (20 mg, 0.024 mmol), 1-fluoro-3-iodo-benzene (104 mg, 0.47 mmol) and piperidine (0.16 ml, 1.6 mmol) are added to a solution of (1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione (0.20 g, 0.71 mmol) in dry N,N-dimethylformamide (2 ml). Formic acid (0.06 ml, 1.6 mmol) is added and the reaction mixture is heated at 50° C. for 2 hours. The reaction mixture is cooled to room temperature, water (1 ml) and dichloromethane (1 ml) are added, and the mixture is stirred for 1 hour. The two phases are separated, the organic phase collected and the solvent is evaporated. The residue is purified by preparative reverse-phase HPLC to give (1RS,2SR,6RS,7SR,8RS)-8-(3-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customThe two phases are separated
  3. customthe organic phase collected
  4. customthe solvent is evaporated
  5. customThe residue is purified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-4394443872004514b123596c6f130ee9
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08754242B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes