Triacetoxyperiodinane → HCID 86761707, compound

HRID 1880603Notes

Reaction equation

HRID 1880603 reaction equation
[OH:1][CH2:2][CH:3]([C:15]1[CH:16]=[C:17]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1)[CH:4]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([O-:12])=[O:11])=[CH:8][CH:7]=1)[CH3:5].[CH3:32]C(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl>[CH3:5][CH:4]([C:6]1[CH:7]=[CH:8][C:9]([C:10]([O:12][CH3:32])=[O:11])=[CH:13][CH:14]=1)[CH:3]([C:15]1[CH:16]=[C:17]([C:21]2[CH:22]=[CH:23][C:24]([O:27][C:28]([F:29])([F:30])[F:31])=[CH:25][CH:26]=2)[CH:18]=[CH:19][CH:20]=1)[CH:2]=[O:1]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86761708HCID 86761708, compound

Product 1

HCID 86761707HCID 86761707, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The intermediate from Step D was subjected to the Suzuki conditions described in EXAMPLE 1 Step A to give methyl 4-{3-hydroxy-1-methyl-2-[4′-(trifluoromethoxy)biphenyl-3-yl]propyl}benzoate as a mixture of diastereomers. LCMS1 3.92 min. (M−H2O)=427. LCMS1 4.08 min. (M−H2O)=427. A DCM (2 mL) solution containing 4-{3-hydroxy-1-methyl-2-[4′-(trifluoromethoxy)biphenyl-3-yl]propyl}benzoate (50 mg, 0.1 μmol) was treated with [1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one] (64 mg, 0.15 mmol). After stirring for 1 hour the solution was concentrated and the residue purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compounds as a mixture of diastereomers. 1H NMR (400 MHz, CDCl3): selected data δ 9.84 (d, J=2.3 Hz); 9.64 (d, J=2.3 Hz); 1.44 (d, J=6.7 Hz); 1.14 (d, J=7.0 Hz). LCMS1 4.11 min. (M+H)=443. LCMS1 4.24 min. (M+H)=443.

Workup

  1. additionas a mixture of diastereomers
  2. customLCMS1 3.92 min. (M−H2O)=427
  3. customLCMS1 4.08 min. (M−H2O)=427
  4. concentrationwas concentrated
  5. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-f8235b7d3f704af2a2af6f614a82f35f
Source dataset
uspto-grants-2012_11
Patent number
US08318760B2

Reaction notes

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